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Cycling the Hudson Valley might not be the first destination that springs to mind for riding in the USA. But we are excited to explain why this is one of the country’s best-kept secrets!

Located just beyond New York City, the Hudson Valley offers an easy escape into nature that feels worlds away from the mayhem of the city that never sleeps.

Home to the mighty Hudson River that winds through peaceful countryside, the landscape is rich in rolling farmland, orchards and forested hills. Combine this with a growing network of bike-friendly trails and a string of charming small towns, and the Hudson Valley has the ingredients you need for a relaxed and scenic cycling holiday.

In this article, we hear from Tommy Struzzieri from Hudson Valley Detours, a luxury bike tour experience created through a partnership between Diamond Mills Resort & Spa and Alpha Win Racing.

  • Diamond Mills is a boutique resort on the banks of the Esopus Creek in Saugerties, featuring elegant accommodation, a farm-to-table restaurant and a relaxing riverside spa.
  • Alpha Win is a leading endurance sports company that organises triathlons and races across the United States. They run tailored cycling packages for guests of Diamond Mills, via their brand Hudson Valley Detours.

With over 40 years of local expertise between them, this guide is jam-packed with local insider knowledge and tips to help you start planning your Hudson Valley cycling tour.

Let’s dive in!

Tommy Struzzieri

Interview with Tommy Struzzieri

Tommy Struzzieri is the founder and CEO of Alpha Win Racing, the organisation behind Hudson Valley Detours’ expertly curated cycling experiences. A Hudson Valley native, Tommy’s passion for endurance sports began in childhood, earning All-American honors in triathlon by age 12. Despite battling major injuries, he went on to compete in Division I track and cross country at Syracuse University.

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As a USA Triathlon Certified Race Director and member of the USA Triathlon Multisport Committee, Tommy brings deep industry knowledge and a commitment to excellence in course design, logistics, and rider experience. His leadership and love for the sport infuse every tour with purpose, challenge, and a sense of adventure, reflecting both the athletic spirit and natural beauty of the Hudson Valley.

Part 1: Why cyclists will love the Hudson Valley

The Hudson Valley is a place where natural beauty, great cycling and rich history come together, making it a fantastic destination for cyclists.

As well as an array of cycling routes (more on that below!), the area has deep historical roots; originally home to Indigenous peoples, it later played a key role in the American Revolutionary War. It’s also the birthplace of the Hudson River School, America’s first art movement, known for its sweeping landscape paintings inspired by the valley’s views.

Today, the Hudson Valley is known as a foodie haven, with world-class restaurants and farmers’ markets, and has become a favourite retreat for creatives and celebrities seeking a quiet escape just a short train ride from New York City.

Picturesque, peaceful countryside

The Hudson Valley is defined by the mighty Hudson River, which cuts through rolling countryside, forested hills, and the dramatic slopes of the Catskill Mountains.

This varied terrain offers flat riverside trails, gentle rolling hills and occasional climbs, making it ideal for cyclists of all abilities. The rural scenery is a joy to experience by bike, with river views, open farmland and wooded lanes found throughout the region.

Top tip! The Hudson Valley landscapes are especially beautiful in autumn, when the rolling hills and riverbanks burst into vibrant shades of red, orange, and gold. Find out more below.

Historic towns and cultural charm

Cycling the Hudson Valley means travelling through some of the oldest and most picturesque towns in New York State. Many date back to the 1700s, with architecture and atmosphere to match.

You’ll ride through Saugerties, Woodstock, and Rhinebeck, all known for their cultural appeal, boutique shopping and top-quality dining experiences.

The Hudson Valley also has a strong creative culture. There are galleries, studios, sculpture parks and festivals throughout the region.

A growing hub for cycling

The Hudson Valley has seen a surge in cycling interest in recent years.

According to the Dutchess County Transportation Council, daily bike traffic on popular rail trails has risen by 67% (source).

The area has responded with major investments in cycling infrastructure, including the 750-mile Empire State Trail, which connects New York City to Canada and passes right through the valley. It’s an encouraging sign of the region’s growing commitment to cyclists,

The Hudson Valley is also home to the Walkway Over the Hudson, which was the world’s longest elevated pedestrian bridge when it opened.

Hudson Valley Detours provides a great bike-friendly base from which to explore the local cycling routes, as well as support from a professional bike team. Find out more below.

Local food and drink scene

The region is a food lover’s paradise. Cyclists can refuel in farm-to-table restaurants, artisan cafés and vibrant farmers’ markets. The valley is also home to world-class wineries, cideries, and craft breweries.

Post-ride, you can sample local produce, from the meat and greens you eat to the bread your butter is on. Diamond Mills also has an in-house pastry chef, and guests enjoy their meals with views of the river or mountains.

Find out more about what food to try below.

Easy access from New York City

The Hudson Valley is just a short journey from Manhattan; it’s only 19 miles from the city’s edge!

This makes it an ideal destination for a weekend escape or extended getaway for urban cyclists looking for space, fresh air and rural scenery.

Train services and major highways make getting here simple and stress-free. More on that below.

Colourful shopfronts along a charming small-town street in Woodstock, New York under vibrant sky

Woodstock main street charm (photo credit: Hudson Valley Detours)

 

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Part 2: An overview of the Hudson Valley from a cyclist’s perspective

Location of the Hudson Valley

The Hudson Valley stretches north from the edge of New York City to the Capital Region around Albany, following the course of the Hudson River and taking in both banks along the way.

It begins just 19 miles from Manhattan in Westchester County and extends roughly 130 miles north to Albany.

Diamond Mills is located in the charming town of Saugerties and sits 100 miles north of Manhattan. Set between the Hudson River and the Catskills, it is perfectly placed for exploring the area’s scenic bike routes and quiet country roads.

See the map below for an overview of some of the key places mentioned in this article. Hover over the map pins to see the names of places.

Terrain

Much of the region features gently rolling hills, ideal for riders who enjoy varied elevation without sustained climbs.

Along the river, especially near towns and popular routes like the Walkway Over the Hudson, you’ll find flatter terrain perfect for relaxed rides and scenic cruising.

This diversity means there’s something for everyone, from mellow riverside routes to more undulating countryside rides that offer a challenge without being too demanding.

Four cyclists riding on a winding forest road surrounded by lush greenery in the Hudson Valley

Riders pedal through a tree-lined country road in the Hudson Valley (photo credit: Hudson Valley Detours)

Roads

Most roads have good-quality surfaces and wide shoulders.

Be aware! Bridges can sometimes feel narrow when traffic is heavy, but they are still safe to cross and include space for cyclists. Two bridges are open to cars that we cross on our tours. These are the Kingston-Rhinecliff Bridge and Rip Van Winkle Bridge. Both bridges have shoulders and should be fine for experienced riders. Our guides ensure all riders cross safely and are on hand to help beginners.

Cyclists are generally warmly welcomed in the Hudson Valley, especially in the smaller towns and villages where bike culture is thriving. Saugerties, Woodstock, and Rhinebeck are all very bike-friendly and where we spend our time in town during the tours. Other towns in the area that are bike-friendly include Poughkeepsie, Beacon, Kingston, Hudson, and more. Lots of them are connected via the large network of rail trails and bike routes.

On Hudson Valley Detours, our guides will always point out any sections that require extra care.

Cycling infrastructure

There is excellent infrastructure for cycling in the Hudson Valley, including several paved river paths and car-free trails.

Popular routes like the Walkway Over the Hudson and the region’s many rail trails are well-maintained, flat, and designed with cyclists in mind. These offer a safe and scenic way to experience the area without the stress of traffic. Find out more about these dedicated bike trails below.

What kind of cyclist is the Hudson Valley for?

The Hudson Valley is a fantastic destination for a wide range of cyclists. Whether you are into road cycling, leisurely rides or gravel adventures, there is an option for you.

Most of the riding is on paved roads and multi-use trails, making it ideal for road cyclists and those looking for a relaxing day out of the city on peaceful country routes.

If you venture into the state parks and mountainous areas, there are also options for gravel and mountain biking. The Hudson Valley is also suitable for families, especially on the dedicated bike and pedestrian paths.

Hudson Valley Detours caters to all fitness levels, with a choice of short, medium or longer rides. Whether you want a gentle cruise or a more challenging ride, we will suggest something to suit you, and e-bikes are also available. We can also adjust our tours to be family-friendly if needed, making it a great choice for cyclists of all ages and abilities.

 

Cycling over the Rip Van Winkle bridge in the Hudson Valley

Cycling over the Rip Van Winkle bridge in the Hudson Valley (photo credit: Hudson Valley Tours)

Do you need a guide to ride the Hudson Valley?

There are many designated cycling routes in the Hudson Valley, so exploring unsupported is possible.

However, riding with a guide in the Hudson Valley offers many advantages.

Local guides know the most scenic, bike-friendly routes and can show you hidden gems and must-see highlights. The guides have extensive experience and knowledge of the region, so they ensure you stay on quiet roads, avoid traffic-heavy areas, and enjoy a smooth, stress-free ride.

Without a guide, navigating can be tricky. The Hudson Valley is one of the oldest settled regions in the United States, and road layouts can be complex. Narrow roads, unclear signage, and less obvious bike routes can make exploring without local knowledge more difficult, especially for first-time visitors.

Hudson Valley Detours offers luxury, all-inclusive cycling tours designed for riders who want more than great cycling. Including guided rides and spa facilities, and treatments. Find out more below.

Part 3: What are the best bases for cycling Hudson Valley?

Saugerties

Located in Ulster County, about 160 kilometres north of New York City, Saugerties sits at the eastern edge of the Catskill Mountains and just west of the Hudson River. Its position between the river and mountains makes it a perfect base for exploring both the rolling terrain of the valley and the more challenging climbs of the Catskills.

Saugerties is a small but vibrant town known for its historic charm, artistic community, and walkable downtown filled with independent shops, cafés, and restaurants. Its riverside setting provides stunning views, and the Hudson River and Esopus Creek add to the scenic appeal. The deck of Diamond Mills sits on an inlet of the Hudson Valley and overlooks the Espous creek and a picturesque waterfall. More on that below.

For cyclists, Saugerties offers the best of both worlds. The surrounding area features quiet country roads, scenic byways, and easy access to both paved and gravel trails. There are a variety of route options starting right from town – for example, pick a gentle riverside loop or a more demanding climb into the Catskills.

Saugerties Lighthouse reflected on the Hudson River at sunset

The historic Saugerties Lighthouse stands at the edge of the Hudson River (photo credit: Hudson Valley Detours)

Woodstock

Tucked into the foothills of the Catskill Mountains, Woodstock is located about 15 kilometres west of Saugerties in Ulster County, around 170 kilometres north of New York City.

World-famous for its artistic heritage and laid-back culture, the town offers a unique blend of creative energy and natural beauty, making it a standout stop on any Hudson Valley cycling trip.

For cyclists, Woodstock is also a rewarding destination. The surrounding landscape features quiet backroads, rolling hills and forested trails, perfect for leisurely rides or more adventurous loops. The routes here are scenic, peaceful and varied.

Woodstock is also home to Overlook Bicycles, the trusted local bike shop partner of Diamond Mills. Their expert team offers reliable service, gear and support, making it easy to get the most from your time on the bike.

Shoppers and cyclists outside cafés and boutiques on a leafy street in Woodstock, New York

Woodstock shops and cafés (photo credit: Hudson Valley Detours)

Rhinebeck

Situated in Dutchess County on the east side of the Hudson River, Rhinebeck lies approximately 150 kilometres north of New York City and just across the river from Saugerties and Woodstock. Its central location in the Mid-Hudson Valley makes it an ideal base for exploring the region on two wheels.

Rhinebeck is one of the Hudson Valley’s most refined and historic towns, known for its 18th-century architecture, tree-lined streets, boutique shops and excellent restaurants. It has long been a popular weekend escape for New Yorkers seeking a blend of charm, culture and countryside. For cyclists, it offers a well-balanced mix of scenery, accessibility and amenities.

The terrain around Rhinebeck is mostly gentle and rolling, with country lanes weaving through farmland, forests and small hamlets. You’ll find quiet, scenic routes that are typically blessed with minimal traffic. It’s also close to several key cycling routes, including the Dutchess Rail Trail, Hudson Valley Rail Trail, and the Walkway Over the Hudson, which connects riders to Highland and beyond via the Empire State Trail. More on these below.

Pedestrians and cyclists at twilight on busy street corner in Rhinebeck, New York beneath US flag

Evening in Rhinebeck town (photo credit: Hudson Valley Detours)

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Part 4: What are the best Hudson Valley rides?

There are a number of dedicated bike trails in the Hudson Valley, meaning cyclists have several great options to choose from when visiting.

The Hudson Valley Detours package at Diamond Mills includes four days of guided tours around the area, the hotel, food, spa services, and a boat ride. The tours are predetermined already. If you book this package they take you on the best rides the region has to offer!

Ashokan Rail Trail, Ulster County

Best for a peaceful ride that feels far from the hustle of urban life

Overview

One of the standout routes in the region is the 18.5-kilometre Ashokan Rail Trail, which opened in 2019. It runs between West Hurley and Boiceville.

This gentle route offers a wide, smooth, crushed-stone trail that runs alongside the Ashokan Reservoir, offering beautiful views with the Catskill Mountains rising in the background.

The Ashokan Rail Trail can be accessed from three public trailheads:

  • Woodstock Dike Trailhead is located at 1285 NY-28 in West Hurley. The Trailhead entrance is 8.5 kilometres west of the NYS Thruway Exit 19 Traffic Circle and approximately 457 metres west of the Stewart’s Shop (by Zena Road).
  • Ashokan Station Trailhead is located at 3045 NY-28 in Shokan. The Trailhead entrance is 18 kilometres west of the NYS Thruway Exit 19 Traffic Circle, across from Mountain Road.
  • Boiceville Bridge Trailhead is located at 5080 Route 28A in Boiceville. The Trailhead entrance is off Route 28, approximately 26.5 kilometres west of the NYS Thruway Exit 19 Traffic Circle. Cold Brook Road is directly across Route 28A from this entrance.

Highlights

  • Lovely views of the Ashokan Reservoir, framed by the Catskill Mountains. Fun fact! The Ashokan is one of the largest reservoirs in the NYC water supply system.
  • Cycling along shaded woodland stretches, these sections are particularly lovely in autumn when the region experiences an explosion of vibrant shades of colour.
  • This trail is also very wide, ranging from 10 to 12 feet in width (3-3.5 metres), which is a lot wider than most bike paths in our region! This means it often feels uncrowded.
Scenic view of a calm lake with the Catskill Mountains in the distance under a partly cloudy sky

Breathtaking lake and Catskill Mountains view in New York (photo credit: Hudson Valley Detours)

 

Walkway Over the Hudson, Dutchess County

Best for cycling on one of the Hudson Valley’s most iconic bridges

Overview

One of the most memorable cycling experiences in the Hudson Valley is the Walkway Over the Hudson, located in Dutchess County. Spanning 1.28 miles, it offers beautiful views of the Hudson River and the surrounding landscape.

It connects the east bank town of Poughkeepsie with Highland on the west, serving as a vital link between major cycling trails. This short but scenic route is ideal for all types of cyclists and forms part of the Empire State Trail, a 750-mile multi-use route stretching from New York City to Canada and Albany to Buffalo. More on that below.

Highlights

  • The bridge boasts panoramic vistas of the Hudson River and valley foliage in autumn from over 60 metres above the water.
  • The trail links the Hudson Valley Rail Trail in Highland with the Dutchess Rail Trail in Poughkeepsie for longer rides.
  • The route is also part of the Empire State Trail, which is the longest multi-use trail in the US!
Walkway over the Hudson

Walkway over the Hudson (photo credit: Hudson Valley Detours)

The Empire State Trail and Hudson Valley Greenway Trail

Best for long-distance cycling adventures through the Hudson Valley and other counties

Overview

The Empire State Trail is the longest multi-use state trail in the U.S., stretching 750 miles from New York City to Canada and Albany to Buffalo. In the Hudson Valley, around 85 % of the trail is off-road, offering a safe and scenic way to explore the region.

The Hudson Valley Greenway Trail forms the core section of this route, connecting communities from Battery Park in Manhattan to Whitehall in the north. The trail is ideal for cyclists, runners, walkers, and even snowshoers in winter, showcasing New York State’s varied and beautiful landscapes.

Hudson Valley Detours cycles on portions of each of these routes.

More bike trails in the Hudson Valley

The following trails all offer cycling on family-friendly bike paths through woodland and rolling hills. All are easily accessible from Diamond Mills, either cycling directly from the hotel or within one hour’s drive:

  • Forest Park Loop
  • Kaaterskill Rail Trail to Kaaterskill Falls
  • Wallkill Valley Rail Trail: New Paltz to Rosendale
  • Catskill Scenic Trail (Delaware County)
  • Catharine Valley Trail (Chemung and Schuyler Counties)
  • D+H Canal/O+W Railway Heritage Corridor (Ulster and Orange Counties)
  • Dutchess Rail Trail (Dutchess County)
  • Fairhaven-Cato Trail (Cayuga County)
  • Genesee Valley Greenway (Allegany, Cattaraugus, Livingston, Monroe and Wyoming Counties)
  • Harlem Valley Rail Trail (Dutchess and Columbia Counties)

Part 5: Practicalities of cycling the Hudson Valley

What is the best time to cycle?

Cycling the Hudson Valley is best done during spring and autumn. This is when Hudson Valley Detours dates are scheduled. Both seasons generally offer ideal riding conditions, with comfortable temperatures and lovely scenery.

Spring

April to early June brings mild weather and blooming landscapes. The roads are usually relatively quiet, the air is fresh, and the scenery is vibrant with new life.

Autumn

Late September to early November is a standout season. The Hudson Valley is famous for its autumn foliage, and cycling through the “leaf-peeping” season is a truly spectacular experience. Expect cooler temperatures, crisp air, and golden views.

Summer

Summer can also be a good time to visit if you’re comfortable with the heat. Days are long and sunny, and the towns are lively with events and open shops. However, some trails offer little shade, so long rides in high temperatures may not be ideal for everyone.

Winter

Be aware! Winter is not suitable for cycling trips. With snow, ice and freezing conditions, it’s best to avoid planning a ride during this time.

Winding country road lined with brilliant orange and yellow fall foliage

Gorgeous autumn foliage (photo credit: Hudson Valley Detours)

What are the best hotels for cyclists in the Hudson Valley?

The Hudson Valley offers a growing number of bike-friendly places to stay.

Depending on the area, there are chain-style hotels like Holiday Inn, cheaper motels, AirBnB/VRBO, and campgrounds. There are also some small-family run hotels, but these are rare.

At the luxury end of the spectrum, Diamond Mills in Saugerties overlooks the scenic Esopus Creek and waterfall. This luxury boutique resort blends comfort, adventure, and relaxation, making it a superb base for a cycling holiday.

As part of the Hudson Valley Detours package, Diamond Mills offers an all-inclusive cycling and wellness retreat, perfect for cyclists looking to explore the region with professional support and high-end hospitality.

Diamond Mills is one of the only resorts in the region offering this level of cycling-specific service. From curated rides to recovery therapies, it’s ideal for cyclists who want more than just a place to stay.

Key features

  • Guided bike tours: Scenic rides through the countryside, over the Hudson River, and around the Ashokan Reservoir. Routes are tailored to your ability and requirements, with 25, 50 or 75 kilometre options available.
  • Bike storage and tune-ups: On-site secure storage and arrival-day tune-up sessions ensure your bike is ready to ride.
  • Bike rentals: Partnered with trusted local shop Overlook Bicycles, offering road bikes and e-bikes.
  • Sports massages and spa recovery: The Waterside Spa offers hydrotherapy, fitness equipment, and recovery-focused treatments for post-ride relaxation.
  • Endurance-supportive dining: BLACKBARN Hudson Valley serves locally sourced, farm-to-table meals designed with active guests in mind.
  • Wellness and sport retreats: Developed in partnership with Alpha Win, combining cycling, wellness, and personalised hospitality for a truly unique experience.

Are there any shops offering Hudson bicycle rentals?

There are a number of bike shops that cater to cyclists in the Hudson Valley. Here are some worth considering:

Overlook Bicycles, Woodstock

Located in the heart of Woodstock, Overlook Bicycles is the Diamond Mills’ trusted local partner. They offer a range of bikes for sale and rent, including e-bikes, and provide expert repairs and fittings. Their proximity to Diamond Mills Resort makes them an ideal choice for guests.

More information

Hudson Bike Co, Highland

Situated near the Walkway Over the Hudson, Hudson Bike Co. offers bike rentals, sales, and repairs. They provide a variety of bikes, including electric options, and are conveniently located for those exploring the Hudson Valley Rail Trail.

More information

TRT Bicycles, Rosendale

A family-owned shop offering rentals, repairs, and professional bike fittings. TRT Bicycles has a fleet of well-maintained bikes suitable for various terrains and provides personalised service to ensure a great riding experience.

More information

How can you get to the Hudson Valley?

The Hudson Valley is well-connected and easy to reach, whether you’re arriving from abroad or travelling domestically.

Airports

For international and domestic travellers, the best options are:

Stewart International Airport (SWF)

Located in New Windsor, this is the closest commercial airport to the central Hudson Valley and a convenient option for reaching destinations like Poughkeepsie or Saugerties.

Albany International Airport (ALB)

Situated at the northern end of the Hudson Valley in Albany, this airport is ideal for those planning to explore the upper Hudson Valley or continue into the Capital Region.

Many visitors also fly into New York City and then travel north by train or car:

  • John F. Kennedy International Airport (JFK)
  • LaGuardia Airport (LGA)
  • Newark Liberty International Airport (EWR)

From any of these, it’s easy to reach Penn Station (for Amtrak) or Grand Central Terminal (for Metro-North) via local transit or shuttle services.

Train travel

The Hudson Valley is served by two major rail lines:

Metro-North Railroad

This commuter rail service runs from Grand Central Terminal in Manhattan along the east side of the Hudson River, with stops in key towns like Tarrytown, Beacon, Poughkeepsie, and Rhinecliff.

Amtrak

Offering longer-distance service from Penn Station, Amtrak trains travel through the Hudson Valley en route to Albany and beyond, stopping in towns like Hudson, Rhinecliff, and Poughkeepsie.

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Part 6: Tips for biking in Hudson Valley

What are the key cycling events in the Hudson Valley?

The Hudson Valley is home to a variety of cycling events throughout the year, including relaxed recreational rides and competitive races.

Some of the top races to watch out for include:

Hudson Valley Triathlon: June

Experience the natural beauty of New York’s Hudson Valley with the Hudson Valley Triathlon. This course begins with a swim in the crystal-clear, spring-fed waters of Williams Lake, followed by a scenic bike ride to the Ashokan Reservoir. It finishes with a run along the historic Wallkill Valley Rail Trail. It’s a perfect blend of athletic challenge and breathtaking surroundings.

More information

Lake George Triathlon: August

Set against the stunning backdrop of the Adirondack Mountains, the Lake George Triathlon Festival offers a truly memorable race experience in one of America’s most scenic locations. Known as the ‘Queen of American Lakes’ and recently voted the cleanest lake in the country, Lake George provides a pristine setting for the swim, with beautiful views throughout the course.

The weekend event blends competitive spirit with a welcoming, family-friendly atmosphere. Don’t miss the exclusive Saturday night VIP dinner cruise aboard a historic Lake George Steamboat, complete with live music and lakeside views.

More information

Alpha Win Saugerties Triathlon: September

This triathlon is a highlight of the local sporting calendar and one of the most scenic triathlons in the northeast. Set against the beautiful backdrop of the Catskill Mountains and Esopus Creek, the event draws athletes of all levels to test their endurance in a welcoming, community-focused atmosphere.

Held annually in Saugerties, the event includes multiple race distances, making it accessible for both seasoned triathletes and those new to the sport. The course features a calm water swim, a rolling bike route through the picturesque countryside, and a scenic run with views of the mountains and creek.

More information

 

What is the food like?

The Hudson Valley is a region rich in local flavour. With its long agricultural heritage, the area is especially renowned for its farm-to-table cuisine, with many restaurants sourcing ingredients directly from local farms.

Towns like Rhinebeck, Woodstock, and Hudson are home to award-winning restaurants, cafés, and bakeries that celebrate the best of the region’s produce. Some of the best restaurants worth booking include:

  • Red Onion, Woodstock
  • Terrapin, Rhinebeck
  • Culinary Institute of America, Hyde Park (there are multiple restaurants to choose from inside)
  • Millhouse Brewery, Poughkeepsie

The valley also boasts a thriving scene of wineries, craft breweries, and distilleries, many of which welcome visitors for tastings. Local favourites include crisp apple ciders, small-batch spirits, and farm-brewed beers, all reflective of the area’s deep-rooted farming traditions.

Food cultures from around the world are represented here too, with influences ranging from Italian and French to Latin American and Asian. It’s not all smart restaurants; food trucks and weekend farmers’ markets are also popular.

  • Local flavours to try: Don’t miss regional specialities like Hudson Valley cheeses, maple syrup, and apple cider doughnuts; perfect for a post-ride treat!
  • Best convenience store options: If you’re stopping mid-ride outside of our guided tours, look for high-protein or high-carbohydrate snacks like energy bars, trail mix, peanut butter sandwiches or bananas. Hydration is key, so grab drinks with electrolytes, especially during the warmer months.
  • On-tour provisions: Our Hudson Valley Detours rides include refreshments and carefully planned nutrition stops, so you’ll always be fuelled and hydrated for your journey.

What gear do I need to bring?

To get the most out of your Hudson Valley cycling holiday, it’s important to pack the right gear. Whether you’re joining a guided tour or riding independently, having the proper kit will help keep you comfortable, safe and prepared for varying conditions.

Some essentials include comfortable clothes for cycling in, including padded shorts and a breathable cycling jersey. Protection from sun and rain is also important, so don’t forget your sunglasses, sun cream and waterproofs!

If you are riding independently, you will also want to bring a helmet, front and rear bike lights, water bottles and a saddle bag to carry your gear.

For a more detailed checklist, head over to our cycling holiday packing list, which covers everything from clothing to bike tools and extras you might not have considered.

Do you need to do any training?

To get the most out of cycling in the Hudson Valley, it helps to have an intermediate level of cycling ability. Riders should be comfortable:

  • Cycling alongside traffic on shared roads, particularly when passing through towns or connecting between trails.
  • Handling rolling and hilly terrain, as many routes feature gentle climbs and descents that require some endurance and bike-handling skills.

You do not need to be an elite athlete, but some basic fitness and confidence on a bike will help you enjoy the ride.

Do you need a car in the Hudson Valley?

While it’s possible to explore parts of the Hudson Valley without a car, having one is very useful, especially if you plan to visit multiple towns or explore routes off the main transit lines.

If you’re staying near the Hudson River, you can make use of Amtrak and Metro-North services, along with local buses and taxis. These towns are more accessible without a vehicle and can serve as good cycling bases.

However, for exploring rural areas, state parks, or quieter trailheads, especially on the west side of the river or in the Catskills, a car will give you the freedom to reach less accessible spots and enjoy more flexibility with your itinerary.

Can you take your bike on public transport?

You can bring your bike on public transport in the Hudson Valley, but there are some rules and limitations to be aware of.

Trains

Trains generally have space for bikes and other large items, though it’s shared and not always specifically designated for bikes.

Be aware! As long as your bike isn’t blocking walkways or doors, it’s usually fine to bring it aboard. Train conductors are typically friendly and can help you find a suitable spot to store it. Some cyclists bring bungee cords to secure their bikes during the ride. While a few trains do offer dedicated bike racks, these are less common, so be prepared to improvise if needed.

Buses

City buses are equipped with front and back-mounted bike racks that can hold up to three adult-sized bicycles. Riders are responsible for loading and unloading their bikes.

For buses doing long travel, like between the Hudson Valley and NYC, their policy is below:

Bicycles may not exceed 8 x 32 x 60 inches and must be securely fastened and wrapped in a box, canvas, or other protective casing to prevent damage should items shift in the baggage compartment. For travellers with connecting schedules, keep in mind that we cannot guarantee your bicycle will be accepted by connecting bus carriers.

Anyone planning to use public transport with a bike should also be mindful of the following:

  • Plan ahead: Check the specific transit agency’s bike policies before your trip, as rules can vary and may change.
  • Peak hours: Try to travel during off-peak times to ensure space for your bike and a more comfortable journey.
  • Bike racks: Familiarise yourself with how to use bus bike racks. Many transit agencies provide instructional videos or guides on their websites.

Highway code and travel information

As ever, it’s a good idea to check current travel information before you book and travel. For UK visitors, the UK government travel information pages for the USA are here.

You should also read and follow the USA NYA Vehicle and Traffic Laws and ensure you have comprehensive travel insurance that covers all the activities you plan on undertaking.

A group of happy cyclists exploring the lush and green Hudson Valley during spring

A group of happy cyclists exploring the lush and green Hudson Valley during spring (photo credit: Hudson Valley Detours)

Part 7: What services do Hudson Valley Detours offer?

Hudson Valley Detours offers a premium, all-inclusive cycling holiday designed for riders who want to explore the Hudson Valley in comfort and style.

In partnership with Alpha Win Racing and hosted at the beautiful Diamond Mills in Saugerties, this five-night retreat blends expert-guided cycling with luxury accommodation, wellness, and local flavour.

What’s included?

  • 4 days of guided cycling through the region’s most scenic routes with experienced local guides. Each ride includes bike transport, support vehicle with refreshments, and repair assistance. Enjoy photo stops, shopping, and sightseeing in towns like Woodstock, Rhinebeck, and New Paltz.
  • 5 nights of boutique accommodation at Diamond Mills, a riverside resort overlooking a waterfall in the heart of Saugerties.
  • Farm-to-table dining prepared by award-winning chefs using fresh, local ingredients.
  • Daily spa treatments at the new Waterside Spa, you can choose from massages, facials, hydrotherapy, and more.
  • Private river cruise and dinner around the historic Saugerties Lighthouse, with drinks served on a secluded dock.

More than a bike tour

Hudson Valley Detours provide a holiday that combines adventure with luxury, supported by a professional team that takes care of every detail. Whether you’re drawn by the scenic rides, the cultural stops, or the chance to relax in a world-class spa, cycling the Hudson Valley with us is an experience you will not find anywhere else.

Our centre-based tours are based at the Diamond Mills, so you only unpack once and enjoy more time relaxing or exploring. Unlike other cycling tours that move to a new hotel each night, our single-hotel approach means more convenience, comfort, and consistency.

Diamond Mills offers the highest level of service, beautiful rooms, and the added indulgence of spa treatments and a private river cruise, amenities rarely found on other cycling tours!

How can I find out more about what you offer?

To find out more or book your place, visit:

Stone and brick Diamond Mills Hotel building at sunset with turrets and landscaped trees in Hudson Valley

Diamond Mills Hotel exterior (photo credit: Hudson Valley Detours)

What’s next?

A huge thanks to Tommy Struzzieri for sharing these insights on cycling the Hudson Valley with us!

Like the idea of biking Hudson Valley? Or perhaps you have already enjoyed the region’s bike trails before? We’d love to hear about your experience of the Hudson cycle routes in the comments below.

Looking for more cycling in the USA? Don’t miss:

For more cycling inspiration in North America, you may also be interested in these guides:

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Tommy Struzzieri

Tommy Struzzieri is the founder and CEO of Alpha Win Racing, the organisation behind Hudson Valley Detours’ expertly curated cycling experiences. A Hudson Valley native, Tommy’s passion for endurance sports began in childhood, earning All-American honors in triathlon by age 12. Despite battling major injuries, he went on to compete in Division I track and cross country at Syracuse University.

As a USA Triathlon Certified Race Director and member of the USA Triathlon Multisport Committee, Tommy brings deep industry knowledge and a commitment to excellence in course design, logistics, and rider experience. His leadership and love for the sport infuse every tour with purpose, challenge, and a sense of adventure, reflecting both the athletic spirit and natural beauty of the Hudson Valley.

Last Reviewed: 07 August 2025

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