NYC to Woodstock (NY-USA)

From big city to Mountain scenery to Artistic Enclave

Easy

Overview

First-time bike tourers located in the NYC metro area, look no further than this route!

This route takes you from the dense urban energy of New York City to the laid-back, artistic enclave of Woodstock, NY, following a mix of historic rail-trails, river valleys, and quiet upstate roads. Much of the journey traces former railroad corridors now preserved as the South County Trailway, North County Trailway, which make up the broader Empire State Trail. You will be treated to long stretches of car-free or low-traffic riding. Ideal for first-time bike tourers, intermediate riders, or confident endurance cyclists who want to power thru this ride in a day; this route blends easy navigation with changing scenery which transitions from city parks to Hudson Valley towns and finally into the foothills of the Catskills.

Perhaps a further selling point is the ready access to public transit along the majority of the route. Riders choose this route for its accessibility, strong trail infrastructure, cultural stops, and the satisfaction of riding from NYC deep into upstate New York without needing advanced bikepacking skills.

Difficulty Explained

Combination of car-free path, modest elevation gains, proximity to resources and public transit access make this trail perfect for beginners. The only section that you will share the road is between Kingston and Woodstock (~10 miles). If you feel uncomfortable, you can always stop in Kingston. More experienced riders can choose to complete this ride in 1-2 days or further challenge themselves by making this an out-and-back route over a long weekend.

Cycle route 18006277 - via bikemap.net

Interactive map showing the complete route. Green marker indicates start point, red marker shows the end point.

Local Businesses

Food/Drink

Casaletto (Elmsford, NY): Family run authentic italian restaurant. Directly off the trail.

Nadine’s (Yorktown Heights, NY): Austrian Restaurant. Directly off the trail.

The Tortilla Project (Baldwin Place, NY): Tacos!. Directly off the trail.

Homestead Marketplace (Stormville, NY): Local spot to buy food and have lunch. Directly off the trail.

Primavera Pizzeria & Family Restaurant (Poughkeepsie, NY): Great pizza!. Directly off the trail.

Bradley Farm and RB Brew,LLC (New Paltz, NY): Picturesque farm with fresh produce. . Directly off the trail.

Rail Trail Cafe (New Paltz, NY): Awesome bike-themed cafe with outdoor seating catering to bikers along the rail trail! Highly Recommend!. Directly off the trail.

Lodging

Suggest Local Businesses

Resources

718 Outdoors (Brooklyn, NY): This is an awesome local bike touring company that offers several supported tours and micro-tours in the Northeast region. While they are not specifically a shop, they are a great resource in case you need information or would like to do a ride with a group of people! . Online Business.

Crank Cycles (Millwood, NY): Great local bike shop. Directly off the trail.

Vintage Fixie (Poughkeepsie, NY): Repair and bike shop with a cool selection of bikes. . .5 mile from the trail .

Hudson Bike Co. (Highland, NY): Bike Shop and Repair. Directly off the trail.

Bicycle Rack (New Paltz, NY): Bike repair shop. Directly off the trail.

Bicycle Depot (New Paltz, NY): Bike repair shop. Directly off the trail.

Springtown Cycles (New Paltz, NY): Bike Shop. Directly off the trail.

Overlook Bicycles Kingston (Kingston, NY): Bike shop and rentals. 5 miles away in Kingston.

Notable Sites + Highlights

NYC - Let's just say you can't miss it!

Van Cortlandt Park - Located in the Bronx. Makes for a nice stop if you're opting for a more leisure ride.

Hudson River Crossing- Soak in views at the Poughkeepsee river crossing.

Mohonk Mountain House- Overpriced but really pretty getaway near New Paltz. This does require about a 5 mile detour from the trail.

Kingston waterfront & Stockade District

Ashokan Reservoir- Large body of water immediately before Woodstock which provides drinking water for NYC. Very scenic and allows for a pretty cool extension to your ride if you would like to soak in more views.

Woodstock Town Center- By this point you've earned some needed relaxation. Enjoy the town center!

Logistics

Transportation To and From

To Start: Getting to NYC; probably the most connected city in USA. You should have no issue here but just ensure your transit method allows for bikes. Driving + Parking to NYC is not recommended but possible.
- Quick Note here: I chose a random starting point in Midtown NYC, but there are a ton of connecting bike paths within the city which you can start from.
To Finish: Getting to Woodstock from within NY, there are more options. Direct bus from NYC. Amtrak serves the nearby town of Kingston. From outside NY, you will likely need to make a connection. Driving to Woodstock is very straightforward.
From Finish to Start: There is a direct bus from NYC to Woodstock. If you need an
Bailing Point: If you need to bail mid-ride, the route does overlap the MTA regional rail in multiple points.

Recommended Gear

Bike: Any bike should suffice for this trail as it is predominantly on asphalt. If you have more time to kill I'd recommend a mountain bike because there are a ton of cool Mtn Bike trails along the route. Rear Rack + Panniers.
Clothing: This is a short enough ride that as long as you look at the weather the day before, just plan for that. That said, I'd always plan for occasional rain.
Safety: Be visible; either with lights or reflective gear, especially on shared roads. Also, having lights will be very useful when camping!
Camping: Definitely not required since this is a short ride BUT some really cool camping spots along the way and a nice way to save some money.
Tools: Multi-tool, spare tubes, patch kit, pump.

Navigation

Signage: Well-signed along the bike paths. Between Kingson and Woodstock (Last ~10 miles) you will need to pull out your GPS to guide you along the best roads.

Resources Along the Way

Lodging: A bit sparse between NYC and Poughkeepsie. Once you hit the Hudson river, you will start to see more lodging options.
Food & Water: Plenty of stops along the way. Never more than 10 miles between towns.
Cell Signal: Spotty in the more rural parts. Make sure you have a 10 mile lookahead in case you lose signal.

Tips

Best Seasons: Late spring through early fall (April–November) for best weather and road conditions. Fall Foliage is gorgeous around late October. Honestly, as long as there's no ice, this can be ridden any time of year.
Emergency Number (USA/Canada): 911 (+1 country code).

Important Warnings

Bring insect repellant: Muggy weather can attract mosquitos

Last 10 miles- Between Kingston and Woodstock will be on shared roads. You can TOTALLY skip this portion if you are not comfortable and end the ride in Kingston.

Route Details

Distance(Miles)

140 mi

Duration

3-5 Days

Elevation(ft)

3000

Countries

United States

Start/End Points

NYC, NY -> Woodstock, NY

Route Format

Point to Point

Bike Lane Types

Bike Path

89%

Separated Bike Lane

Shared Lane

11%

External Resources

Empire State Trail

South County Trailway - Wiki

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