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.
Last updated: May 13, 2026
4.8
(5)
60
riders
40.8km
02:21
100m
100m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
35
riders
80.3km
04:46
450m
450m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(2)
25
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(4)
15
riders
23.1km
01:21
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
10
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Vineyard Haven
The cycle paths are well developed and there is little traffic.
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A very beautiful beach with white sand and clear water.
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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.
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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
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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.
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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.
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


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