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Road cycling routes
United States
Massachusetts
Dukes County

Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark

Routes
Road cycling routes
United States
Massachusetts
Dukes County

Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark

Moderate

5.0

(6716)

14,543

riders

Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark

02:39

64.4km

300m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: May 8, 2026

Tips

Includes a segment in which cycling is not permitted

After 2.45 km for 62 m

Waypoints

A

Start point

Bus stop

Get Directions

1

6.06 km

Joseph Sylvia State Beach

Highlight • 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 …

Tip by

13.9 km

East Chop Cliffs

Nature Reserve

18.0 km

Lagoon Bridge Park & Boat Landing

Nature Reserve

4

19.3 km

Vineyard Haven Harbor

Highlight • Structure

Vineyard Haven Harbor has been the main port for Vineyard for over 300 years. You'll spot traditional sailboats bobbing in the water – hundreds of boats use the harbor today.

Tip by

5

41.9 km

Chilmark

Highlight • Settlement

Chilmark is a charming, historic town with a lovely center that is home to New England Treasures. It is a lively spot, especially during March when the Martha’s Vineyard Film …

Tip by

6

50.0 km

West Tisbury

Highlight • Settlement

Dive into the rich history of West Tisbury, a charming New England town settled by English pioneers in 1669. With cute shops, historic buildings, and mills, it's not just a town; it's the island's agricultural heartland.

Tip by

50.4 km

Old Millpond

Lake

B

64.4 km

End point

Bus stop

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Way Types & Surfaces

Way Types

40.9 km

16.7 km

6.74 km

Surfaces

58.4 km

5.83 km

128 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (60 m)

Lowest point (0 m)

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Weather

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Today

Saturday 11 July

26°C

17°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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Description

If you're looking for a quintessential Martha's Vineyard road cycling experience that blends coastal beauty with charming island towns, the Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark is a fantastic choice. This moderate 40.0-mile (64.4 km) route, with 978 feet (298 metres) of elevation gain and an estimated duration of 2 hours and 38 minutes, offers a diverse ride perfect for those who want to see a lot of the island's "down-island" highlights without an overly strenuous climb. It's an ideal pick for a scenic day out on two wheels.

What to expect on Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark

As you embark on this loop, you'll quickly find yourself immersed in the island's diverse landscapes. The route features long, flat stretches, particularly along Joseph Sylvia State Beach, where you'll cycle with stunning views of the Atlantic Ocean and Nantucket Sound, separated by the barrier beach. You'll even cross the famous American Legion Memorial Bridge, known as "Jaws Bridge," a true island icon. Beyond the coast, the trail weaves through sections of scrub oak and pine forests, offering a change of scenery before heading towards the bustling Vineyard Haven Harbor. While generally moderate, expect some gentle undulations and occasional elevation gain, making it suitable for cyclists with good fitness looking for a rewarding ride.

Planning your visit

Starting your ride from Katama Airpark is convenient, as it's a known hub for bike tours and rentals. The route primarily uses paved bike paths, which are often separated from vehicular traffic, making for a safer cycling experience. However, be aware that some segments might be on shared roads or have cracked surfaces. The best time to cycle Martha's Vineyard is typically during the shoulder seasons to avoid peak summer crowds, though the island is beautiful year-round.

Trail details

  • Distance: 40.0 miles (64.4 km)
  • Elevation gain: 978 feet (298 metres)
  • Difficulty: moderate
  • Estimated time: 2 hours and 38 minutes

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Road ride to Aquinnah Headlands Preserve – South Head

03:34h

79.3km

370m

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