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Road ride to Aquinnah Headlands Preserve – South Head
79.3km
03:34
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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By Fede from komoot
·
Updated May 10, 2026
If you've ever tried to plan road cycling in Dukes County, you know how quickly the options can become overwhelming. With so many paths and coastal roads, it's tough to tell which routes are genuinely worth your precious time and effort, and which are just filler. That's where we come in. Our komoot community has ridden, reviewed, and mapped these routes, allowing us to cut through the noise and give you a curated shortlist of the very best. We've done the legwork so you don't have to.
Road cycling in Dukes County, primarily centered on Martha's Vineyard, offers a truly unique experience. You'll find everything from leisurely, flat spins connecting charming towns to more challenging, hilly routes that reward you with dramatic coastal views. The island's diverse terrain means you can easily switch between shaded forest paths and open oceanfront stretches. While the dedicated bike paths are extensive, especially on Martha's Vineyard, expect some areas, particularly "up-Island" towards Aquinnah, to offer a more demanding ride with noticeable climbs.
If you only do one ride, make it the Road ride to Aquinnah Headlands Preserve – South Head. At 49.3 miles (79.3 km) with 1,215 feet (370 m) of climbing, it's a moderate challenge that delivers incredible payoff with its sweeping coastal vistas. For something a bit more relaxed, especially if you're looking for an easy introduction, the Edgartown Beach loop is a fantastic choice at 15.5 miles (24.9 km), offering lovely coastal scenery without the big climbs. Dive into our collection and discover why more than 1,500 road cyclists have already explored Dukes County with komoot.
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Road ride to Aquinnah Headlands Preserve – South Head | 79.3 km | 370 m | Moderate |
| Edgartown Beach loop | 24.9 km | 60 m | Easy |
| Around Martha's Vineyard – road cycling in MA | 32.4 km | 140 m | Easy |
| Vineyard Haven Harbor – Aquinnah Headlands Preserve loop from Vineyard Haven | 62.3 km | 410 m | Moderate |
| Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark | 64.6 km | 300 m | Moderate |
| Historic Edgartown – Joseph Sylvia State Beach loop from Tisbury Meadow Preserve | 45.4 km | 120 m | Moderate |
| Sweetened Water Pond loop from Edgartown | 45.5 km | 120 m | Easy |
| Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven | 29.0 km | 70 m | Easy |
| Joseph Sylvia State Beach – Harts Harbor loop from Edgartown | 16.0 km | 30 m | Easy |
| Harts Harbor – Joseph Sylvia State Beach loop from Felix Neck Preserve | 20.9 km | 70 m | Easy |
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Sign up for free79.3km
03:34
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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24.9km
01:18
60m
70m
The Edgartown Beach loop offers a delightful coastal cycling experience on Martha's Vineyard, perfect for a relaxed outing. You'll glide along mostly paved surfaces, enjoying extensive views of State Beach and Sengekontacket Pond. A highlight is crossing the famous "Jaws Bridge," where you'll have unobstructed vistas of the pond on one side and Nantucket Sound on the other, making for a truly scenic ride.
This easy road cycling route covers 15.5 miles (24.9 km) with a gentle 210 feet (64 metres) of elevation gain, typically taking about 1 hour and 17 minutes to complete. It's an excellent choice for families or anyone seeking a leisurely ride without significant climbs. Parking is generally available in Edgartown, but consider an early start during busy seasons to secure a spot.
This loop is a favorite among local cyclists for its combination of ease, beautiful coastal scenery, and cultural landmarks. It's part of Martha's Vineyard's dedicated bike path network, providing a safe and enjoyable experience away from vehicle traffic. The route is particularly well-suited for those looking for family-friendly cycling options on the island.
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32.4km
01:22
140m
140m
Easy road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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62.3km
02:53
410m
410m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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64.6km
02:39
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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45.4km
01:56
120m
120m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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45.5km
01:59
120m
120m
The Sweetened Water Pond loop from Edgartown offers a delightful road cycling experience, guiding you through a mosaic of Martha's Vineyard's natural beauty. You'll glide past serene forests, expansive farm fields, and open meadows, with the highlight being the tranquil Sweetened Water Preserve, where you can soak in views of Sweetened Water Pond and Beetle Pond. The terrain is mostly well-paved and generally flat, making for a smooth and enjoyable ride.
This easy 28.1-mile (45.2 km) route with a modest 394 feet (120 metres) of elevation gain is typically completed in about 1 hour and 56 minutes, making it an ideal choice for a leisurely outing. Starting directly from Edgartown, the loop is easily accessible and suitable for various fitness levels. It's a popular choice for those seeking a scenic and manageable bike ride on the island.
Historically, the Sweetened Water Preserve and surrounding lands were part of a dairy farm, with Holstein and Guernsey cattle once using the ponds as watering holes. Today, the area showcases successful conservation efforts, with restored open grasslands blending into a scenic corridor of fields. This blend of natural beauty and agricultural heritage makes the route particularly interesting for exploring the island by bike.
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29.0km
01:08
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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16.0km
00:39
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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20.9km
00:48
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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This historic lighthouse was built in 1878 and is maintained by the Martha's Vineyard Museum. The museum runs $5 sunset tours during the summer, and the lighthouse is also available to be rented out as a venue for weddings and other events.
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The cycle paths are well developed and there is little traffic.
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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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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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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.
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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 Festival is held here. Chilmark boasts the highest point on Martha's Vineyard.
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Dukes County, primarily Martha's Vineyard, offers a diverse range of terrain. You'll find extensive networks of mostly flat, paved paths, especially in 'down-Island' areas connecting towns like Vineyard Haven, Oak Bluffs, and Edgartown. For more challenging rides, 'up-Island' communities such as West Tisbury, Chilmark, and Aquinnah feature hillier and curvier routes. Many paths also offer scenic coastal views.
Yes, Dukes County is very family-friendly. There are approximately 44 miles of 'down-Island' bike trails that are mostly flat and suitable for recreational and younger cyclists. An excellent easy option is the Edgartown Beach loop, which is 15.5 miles (24.9 km) and offers coastal scenery. Another easy route is Sweetened Water Pond loop from Edgartown, covering 45.5 km.
Many routes offer stunning views and pass by significant landmarks. You can cycle past the famous gingerbread cottages in Oak Bluffs and stop at the East Chop Light. The six-mile path between Oak Bluffs and Edgartown along Beach Road provides scenic views of Joseph Sylvia State Beach and Sengekontacket Pond. Inland, the Manuel F. Correllus State Forest offers over 14 miles of trails amidst lush greenery. You might also encounter Historic Edgartown, a charming town with a rich history.
There are over 45 road cycling routes available in Dukes County on komoot, catering to various skill levels. This includes 29 easy routes and 17 moderate routes, ensuring options for everyone from beginners to more experienced cyclists.
The area is highly rated by the komoot community, with an average score of 4.25 stars from over 8 reviews. Cyclists often praise the diverse island landscapes, the prevalence of coastal paths, and the charming towns. Over 800 road cyclists have used komoot to explore Dukes County's varied terrain, highlighting its appeal.
Yes, for those seeking a longer ride, the entire perimeter of Martha's Vineyard can offer rides of 60+ miles. A moderate route to consider is Road ride to Aquinnah Headlands Preserve – South Head, which is 49.3 miles (79.3 km) and takes approximately 3 hours 34 minutes, leading to the Aquinnah Headlands Preserve with coastal views. Another moderate option is the Vineyard Haven Harbor – Aquinnah Headlands Preserve loop from Vineyard Haven, covering 62.2 km.
Yes, the Vineyard Transit Authority (VTA) public buses are equipped to accommodate bicycles, making it convenient to explore different parts of the island without having to cycle the entire distance. This allows for more flexible route planning.
Martha's Vineyard offers appealing cycling conditions throughout much of the year. The summer months are popular, but spring and fall often provide pleasant temperatures and fewer crowds, making them ideal for exploring the island's diverse landscapes and coastal routes.
Yes, many routes in Dukes County are designed as loops, allowing you to start and end in the same location. Examples include the Edgartown Beach loop and Around Martha's Vineyard – road cycling in MA, which leads through diverse island landscapes. The Historic Edgartown – Joseph Sylvia State Beach loop from Oak Bluffs is another excellent circular option.
Coastal views are a highlight of road cycling in Dukes County. The path between Oak Bluffs and Edgartown along Beach Road offers stunning vistas of State Beach and Sengekontacket Pond. East Chop Drive also provides picturesque views with less car congestion. Many routes, such as Joseph Sylvia State Beach – Vineyard Haven Harbor loop from Katama Airpark, incorporate significant stretches along the coastline.
While many conservation areas are primarily for hiking, road cyclists can enjoy routes that pass by or through areas like the Manuel F. Correllus State Forest, which features well-marked bike trails amidst lush greenery. Routes leading to areas like Aquinnah Headlands Preserve also offer access to natural beauty and coastal views.


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