Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Cycling routes
United States
Massachusetts
Dukes County

Vineyard Haven

The best cycling routes around Vineyard Haven

4.8

(57)

908

riders

38

rides

Touring cycling around Vineyard Haven offers diverse landscapes, from coastal paths and sandy beaches to lush woodlands and nature preserves. The region features a mix of paved bike paths and scenic roads, providing varied terrain for cyclists. While many routes are flat and family-friendly, some areas present rolling terrain with gentle climbs.

Best touring cycling routes around Vineyard Haven

  • The most popular touring cycling route is Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven, a 25.2…

Last updated: May 13, 2026

4.8

(5)

60

riders

#1.

Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven

40.8km

02:21

100m

100m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate with device

Send to Phone

Save

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(4)

15

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
Sign up for free to see 34 more rides around Vineyard Haven.

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

Popular around Vineyard Haven

Hiking around Vineyard Haven

Road Cycling Routes around Vineyard Haven

Running Trails around Vineyard Haven

Tips from the Community

Jan
June 22, 2025, Menemsha Bike Ferry

Ferry runs Sat/Sun 9-5 on request

0

0

Ulrike
August 19, 2024, Harts Harbor

The cycle paths are well developed and there is little traffic.

Translated by Google

0

0

A very beautiful beach with white sand and clear water.

Translated by Google

0

0

A beautiful spot and a great starting point for bike tours. There are plenty of rental companies there. E-bikes are quite expensive though, ~$75 per day.

Translated by Google

0

0

Moshup Beach, also known as Aquinnah Public Beach, borders Gay Head Beach, which lies below the cliffs. https://www.savebuzzardsbay.org/places-to-go/moshup-beach/ In August 1991, Hurricane Bob altered much of Martha's Vineyard's coastline. Moshup Beach now has clay cliffs as well. Before the storm, there were only sand dunes here. https://vineyardgazette.com/news/1991/08/30/changing-island-face-storms-surgical-srike

Translated by Google

2

0

Matthew
February 19, 2024, Harts Harbor

Sandwiched between Joseph Sylvia State Beach and the Felix Neck Conservation Area, Harts Harbor is a large body of water. It's actually an extension of Sengekontacket Pond and is nice to look at as you ride along the bike path.

0

0

Amy
February 19, 2024, Joseph Sylvia State Beach

With soft, golden sand and shallow water, Joseph Sylvia State Beach is a popular hangout spot on Martha's Vineyard. The beach extends 5 miles (8 km) between Oak Bluffs and Edgartown. It's public and not privately owned like many of the island's beaches. On one side, the Atlantic Ocean glistens into the horizon and on the other, Cow Bay stretches around the coast. It's popular for windsurfing and kitesurfing when the weather is right.

0

0

Matthew
February 19, 2024, Farm Pond

Farm Pond looks more like a lake from the bike path with how big it is. You also get a pretty good view of the surrounding wetlands and the ocean on the other side of the highway from here.

0

0

Frequently Asked Questions

What kind of terrain can I expect when touring cycling around Vineyard Haven?

Vineyard Haven offers a diverse range of terrain for touring cyclists. You'll find a mix of paved bike paths and scenic roads. Many routes are relatively flat and family-friendly, especially along the coast. However, for those seeking more challenge, the 'up-Island' communities of West Tisbury, Chilmark, and Aquinnah feature rolling and hilly roadways. The Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven, for example, is a moderate route with some elevation changes.

Are there easy touring cycling routes suitable for families or beginners?

Yes, Vineyard Haven has many easy and family-friendly touring cycling routes. The region boasts over 40 miles of bike paths, with many routes being flat and suitable for all skill levels. An easy option is the Joseph Sylvia State Beach – Historic Edgartown loop from Oak Bluffs, which is 17.7 miles (28.5 km) and takes about 1 hour 37 minutes to complete. The 6-mile journey between Vineyard Haven and Oak Bluffs along East Chop Drive is also known for its minimal traffic and suitability for families.

What are the most scenic natural features to see while cycling in Vineyard Haven?

Cyclists can enjoy stunning coastal views and beaches, such as along East Chop Drive or the West Chop Loop, which offer vistas of Vineyard Sound and Falmouth. Joseph Sylvia State Beach provides 5 miles of scenic riding between Oak Bluffs and Edgartown. For a more forested experience, the West Chop Woods Preserve and the Caroline Tuthill Preserve offer trails through lush woodlands and marshland. You can also visit Lake Tashmoo Beach for sandy shores and views.

Are there any circular touring cycling routes in Vineyard Haven?

Yes, many touring cycling routes in Vineyard Haven are designed as loops, allowing you to start and end in the same location. A popular moderate circular route is the Joseph Sylvia State Beach – Historic Edgartown loop from William Street Historic District, covering 34.8 miles (55.9 km). Another easy loop is the Nobska Lighthouse loop from Oak Bluffs, which is about 8.5 km.

What interesting landmarks or places can I explore along the cycling routes?

Beyond the natural beauty, you can explore several landmarks and charming towns. The Historic Edgartown is a popular destination, often included in loops like the Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven. You can also cycle past the East Chop Light, the West Chop Lighthouse, or visit Nobska Point Light. Downtown Vineyard Haven itself offers quaint shops, art galleries, and cafes in historic 19th-century buildings.

How many touring cycling routes are available around Vineyard Haven?

There are nearly 40 touring cycling routes available around Vineyard Haven, catering to various skill levels. This includes 22 easy routes, 15 moderate routes, and 1 difficult route, ensuring options for everyone from beginners to more experienced cyclists.

What do other touring cyclists enjoy most about cycling in Vineyard Haven?

The touring cycling routes in Vineyard Haven are highly rated by the komoot community, with an average score of 4.8 stars from over 50 reviews. Reviewers often praise the diverse landscapes, from scenic coastal paths and sandy beaches to lush woodlands, and the well-maintained network of bike paths that connect charming towns.

Is public transport available to access the bike trails, and can I bring my bike?

Yes, the Vineyard Transit Authority (VTA) buses are equipped with bike racks, offering a convenient way to access various parts of the island's cycling network. This provides flexibility for longer rides or if you wish to combine cycling with public transport.

Are there any wildlife areas or nature preserves accessible by bike?

Absolutely. The Felix Neck Wildlife Sanctuary, located a short distance from Vineyard Haven, offers 4 miles of trails through woodlands, meadows, ponds, and salt marsh, perfect for nature lovers and birdwatching. Additionally, the West Chop Woods Preserve and the Caroline Tuthill Preserve provide opportunities to cycle through lush woodlands and explore natural habitats. You can also find Salt Pond Acres Wildlife Area and Salt Pond Areas Bird Sanctuary.

Can I cycle along the harbor in Vineyard Haven?

Yes, you can certainly cycle along the harbor in Vineyard Haven. The town's picturesque harbor is a central point, and cyclists can enjoy routes that offer panoramic views of the harbor and the distant Elizabeth Islands. The Vineyard Haven Harbor loop from Oak Bluffs is an easy 10.4 km route that allows you to experience the waterfront.

What is the best time of year for touring cycling in Vineyard Haven?

While Vineyard Haven offers cycling opportunities year-round, the spring, summer, and early fall months generally provide the most pleasant weather for touring. During these seasons, you can fully enjoy the coastal breezes, lush greenery, and vibrant activity of the island. It's always a good idea to check local weather forecasts before heading out.

Most popular routes around Vineyard Haven

Easy hikes around Vineyard Haven

Most popular attractions around Vineyard Haven

Places to see

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 Cycling routes in other regions.

South Beach State ParkEdgartownManuel F. Correllus State ForestOak Bluffs

Nearby adventure guides

Things to Do around Oak Bluffs

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