Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Road cycling routes
United States
New York
Dutchess County

Pine Plains

The best road cycling routes around Pine Plains

5.0

(1)

67

riders

20

rides

Road cycling routes around Pine Plains offer a compelling mix of natural beauty and diverse terrain in Dutchess County, New York. The area is characterized by scenic landscapes, including prominent hills like Stissing Mountain, and extensive woodland scenery. Cyclists can find mostly well-paved surfaces across a network of routes that traverse both open plains and more undulating sections. This region provides varied road cycling experiences, from gentle rides through valleys to routes with significant elevation gains.

Best road cycling routes around Pine Plains

  • The most popular road cycling route is Roadbike loop from Town of Pine Plains, a 12.6 miles (20.3 km) trail that takes 1 hour 4 minutes to complete. This easy route offers a pleasant ride through the local countryside.
  • Another top favourite among local road cyclists is Rudd Pond – Rail trail bridge loop from Town of Pine Plains, a moderate 51.9 miles (83.6 km) path. This route features varied terrain and includes a significant elevation gain of over 2,600 feet (800 meters).
  • Local road cyclists also love the Roadbike loop from McGee Hill, a 39.3 miles (63.2 km) trail leading through scenic rural landscapes, often completed in about 3 hours 2 minutes.
  • Road cycling around Pine Plains is defined by rolling hills, open plains, and dense woodlands. The network offers options for different ability levels, from easy loops to more challenging rides with substantial climbs.
  • The routes in Pine Plains are highly rated by the komoot community with an average score of 5.0 stars from a few reviews. More than 70 road cyclists have used komoot to explore Pine Plains's varied terrain.

Last updated: July 12, 2026

13

riders

#1.

Snake Hill loop from Thompson Pond

27.9km

01:21

280m

280m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Navigate with device

Send to Phone

Save

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

5.0

(1)

5

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

3

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
Sign up for free to see 16 more rides around Pine Plains.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Tips from the Community

Alex Tray
June 8, 2024, Rail trail bridge

View of a pond and wildlife

0

0

Buttercup Farm Audubon Sanctuary is a wildlife haven, spanning 641 acres. The diverse landscapes are home to birds and many other animals. Take in the views of meadows, grasslands, second-growth woods, mature woods, and more. Keep an eye out for great blue herons, wood ducks, and more of the over 80 species of birds that call Buttercup Farm Audubon Sanctuary home.

0

0

Alex
January 26, 2024, Rudd Pond

Sitting directly adjacent to the road, this pond makes for an impressive sight whilst cycling alongside it. Keep your eyes peeled for the bird species that inhabit the surrounding woodland.

0

0

If you are into history, this is for you. This house was a hotel (1798-1849) and doctor's office (1798-1822), and then a Post office until 1906.

0

0

Frequently Asked Questions

How many road cycling routes are available in Pine Plains?

Pine Plains offers a robust network of over two dozen road cycling routes, catering to various skill levels. You'll find everything from easy loops to more challenging rides with significant elevation gains.

What kind of terrain can I expect on road cycling routes in Pine Plains?

The terrain in Pine Plains is quite diverse, featuring rolling hills, open plains, and dense woodlands. While many routes offer mostly well-paved surfaces, you can expect varied elevation changes, including significant climbs, especially on routes like the Rudd Pond – Rail trail bridge loop from Town of Pine Plains.

Are there any easy road cycling routes suitable for beginners in Pine Plains?

Yes, Pine Plains has several easy routes perfect for beginners or those looking for a relaxed ride. An excellent option is the Roadbike loop from Town of Pine Plains, which is 20.3 km long with minimal elevation gain, offering a pleasant ride through the local countryside.

What are some scenic viewpoints or landmarks I can see while cycling in Pine Plains?

Road cycling in Pine Plains offers numerous scenic views. You can enjoy the dramatic vistas from Stissing Mountain, which provides panoramic views extending to neighboring states on a clear day. The ecological richness of Thompson Pond and the overall beauty of the Wappinger Creek Valley also contribute to the aesthetic appeal of the rides. Routes often pass through beautiful woodland scenery and vast plains.

Are there challenging routes for experienced road cyclists in Pine Plains?

Absolutely. For experienced cyclists seeking a challenge, Pine Plains offers routes with substantial elevation gains. The Rudd Pond – Rail trail bridge loop from Town of Pine Plains, for instance, is a moderate 83.6 km path with over 800 meters of elevation gain. Other routes like the Roadbike loop from McGee Hill also provide significant climbs.

What do other road cyclists say about the routes in Pine Plains?

The road cycling routes in Pine Plains are highly regarded by the komoot community, holding an average score of 5.0 stars. Cyclists often praise the varied terrain, from gentle loops to challenging climbs, and the beautiful natural scenery that enhances the riding experience.

Can I find loop routes for road cycling in Pine Plains?

Yes, many of the road cycling routes in Pine Plains are designed as loops, allowing you to start and end your ride in the same location. Examples include the Roadbike loop from Town of Pine Plains and the Hunns Lake – Carpenter Hill loop from McGee Hill.

What is the best time of year for road cycling in Pine Plains?

While specific weather conditions vary, the region's natural beauty, including woodlands and plains, suggests that spring, summer, and fall would offer the most pleasant cycling conditions. These seasons provide comfortable temperatures and vibrant scenery, making for an enjoyable ride.

Are there any historical points of interest along the cycling routes?

Yes, the area around Pine Plains has historical significance. For example, the Stage Inn Historical Sign – Snake Hill loop from Green Hill route suggests that you might encounter historical markers or sites like the Stage Inn, offering a glimpse into the region's past while you ride.

Where can I find information about parks and recreation in Pine Plains?

For more details on local parks and recreational facilities in Pine Plains, you can visit the official town website: pineplains-ny.gov/parks-recreation/.

What makes Pine Plains a unique destination for road cycling?

Pine Plains stands out due to its compelling mix of natural beauty, diverse terrain, and dedicated cycling routes. The presence of unique geological features like Stissing Mountain, the ecological significance of Thompson Pond, and the overall scenic beauty of the Wappinger Creek Valley create a distinctive and rewarding cycling experience.

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Road cycling routes in other regions.

ArlingtonShorehavenBrinckerhoffHopewell JunctionNew HamburgChelsea CovePawlingHavilandTitusvilleFishkillMyers CornerPoughkeepsiePleasant ValleyWappingers FallsMerritt ParkRhinecliffTaconic State Park – Rudd Pond AreaUpper Red HookHyde ParkRed Oaks MillWest Mountain State ForestFairviewMarist CollegeHillside LakeBard CollegeTivoliNew HackensackCrown HeightsRed HookWingdaleSpackenkillSalt PointJames Baird State ParkMillertonMacdonnell HeightsFreedom PlainsVassar CollegeAmeniaRhinebeckWassaicBarrytownBeaconOgden Mills And Ruth Livingston Mills State ParkStaatsburgDover PlainsMargaret Lewis Norrie State ParkMillbrook

Nearby adventure guides

Things to Do in Lake Taghkanic State Park

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy