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Massachusetts

Dukes County

The best walks and hikes in Dukes County

4.9

(22)

169

hikers

14

hikes

Hikes in Dukes County explore the islands of Martha's Vineyard and the Elizabeth Islands. The region is characterized by coastal paths, serene beachfronts, and tranquil woodlands. The terrain is relatively flat, with trails winding through conservation lands, wildlife sanctuaries, and alongside salt marshes and ponds.

Best hiking trails in Dukes County

  • The most popular hiking route is Brickyard Site – Prospect Hill loop from Menemsha, a 4.3 mile (7.0 km) trail that takes about 1 hour 55 minutes to complete. This route leads to the historic brickyard site and offers views from Prospect Hill.
  • Another top favourite among local hiking enthusiasts is Prospect Hill – Brickyard Site loop from Chilmark, a moderate 7.6 mile (12.3 km) path. The trail traverses coastal habitats within the Menemsha Hills Reservation.
  • Local hiking enthusiasts also love the Edgartown Pond Lot loop from Edgartown, a 1.4 mile (2.2 km) trail leading through woodlands near the pond, often completed in about 35 minutes.
  • Hiking in Dukes County is defined by coastal views, sandplain grasslands, and woodland trails. The network of paths provides accessible options for different ability levels, from short loops to longer coastal hikes.
  • The routes in Dukes County are highly rated by the komoot community with an average score of 4.9 stars from more than 10 reviews. More than 130 hikers have used komoot to explore Dukes County's varied terrain.

Last updated: May 12, 2026

5.0

(1)

6

hikers

#1.

Brickyard and Prospect Hill Loop

5.15km

01:25

90m

80m

Hike the easy 3.2-mile Brickyard and Prospect Hill Loop for scenic views, historic sites, and a peaceful escape in Menemsha Hills Reservatio

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Easy

Hike the easy 1.2-mile Sepiessa Point Reservation Trail on Martha's Vineyard, offering diverse landscapes and Tisbury Great Pond views.

Easy
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1

hikers

Hike the easy 1.3-mile Fulling Mill Brook Preserve Trail on Martha's Vineyard, exploring lush woods and unique glacial boulders.

Easy

Hike the easy 2.1-mile Waskosim's Rock Reservation Trail, exploring diverse landscapes and the historic Waskosim's Rock on Martha's Vineyard

Easy

Hike the 14.3-mile Vineyard Haven to Chappaquiddick Bike Path, a difficult route with 211 feet of gain, offering diverse island scenery.

Hard

Explore the easy 3.0-mile Trade Wind Fields and Farm Pond Preserves Loop on Martha's Vineyard, featuring diverse woodlands, meadows, and pon

Easy

Explore the easy 0.5-mile Maria Daggett and Red Blue Trail in Cedar Tree Neck Sanctuary, a short hike with minimal elevation gain.

Easy

Hike the easy 1.0-mile Raft and Marl Ponds Loop in Great Rock Bight Preserve, offering a quick outdoor escape with minimal elevation gain.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around Dukes County

Hiking in Manuel F. Correllus State Forest

Hiking around Vineyard Haven

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Road Cycling Routes in Dukes County

Cycling in Dukes County

Running Trails in Dukes County

Tips from the Community

Zachary
September 19, 2024, East Chop Lighthouse

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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Ulrike
August 19, 2024, Harts Harbor

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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Comprehensive information about 'The Brickyard' can be found at: https://thetrustees.org/place/the-brickyard/ https://mvmagazine.com/news/2020/08/20/what-remains-be-seen

Translated by Google

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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.

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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.

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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.

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Alexandra Pavia
February 3, 2024, Menemsha

Menemsha is a quaint fishing village nestled in Chilmark. Situated on the east coast of Menemsha Pond, right by the opening into Vineyard Sound, this village is steeped in history. The iconic harbor, serving as a departure point for local fishermen, including those from multi-generational fishing families, and charter boats heading to the Elizabeth Islands.

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Frequently Asked Questions

Are there many hiking trails in Dukes County?

Yes, there are over 25 marked hiking trails across Dukes County. The region offers a great variety, from short, easy loops perfect for a quick stroll to more moderate coastal treks. Most trails are well-maintained and explore the island's diverse landscapes, including woodlands, beaches, and wildlife sanctuaries.

What do other hikers enjoy most about the trails in Dukes County?

The area is highly rated by the komoot community. Hikers frequently praise the stunning coastal scenery, the well-preserved natural habitats, and the tranquility of the trails. The combination of woodland paths leading to secluded beaches is a particularly celebrated feature of hiking on Martha's Vineyard.

Are there any easy, family-friendly hikes on Martha's Vineyard?

Absolutely. The terrain in Dukes County is relatively flat, making it ideal for families. A great option is the Edgartown Pond Lot loop from Edgartown, a short and gentle walk. Another popular choice is the Caroline Tuthill Preserve, known for its lovely, easy-to-follow trail loops through the woods.

Where can I find the best coastal views while hiking?

For dramatic coastal scenery, head to the Aquinnah Cliffs Overlook, a highly-regarded spot offering sweeping views of the Atlantic and the iconic clay cliffs. For a trail experience with great views, the hike within Menemsha Hills is a local favorite, leading you up to vistas overlooking the harbor and coastline.

Are dogs allowed on the hiking trails in Dukes County?

Dog policies vary by preserve and season. Many trails managed by the Martha's Vineyard Land Bank, such as those at Menemsha Hills and Great Rock Bight Preserve, typically allow leashed dogs. However, wildlife sanctuaries like Felix Neck and Long Point have stricter rules to protect nesting birds and other fauna, often prohibiting dogs, especially during certain times of the year. Always check the specific regulations for the trail you plan to visit before you go.

What are some good trails for birdwatching?

Dukes County is a fantastic destination for birdwatchers. The Felix Neck Wildlife Sanctuary is a premier location, with four miles of trails through salt marshes and meadows where you can spot ospreys and herons. Long Point Wildlife Refuge is another excellent choice, offering opportunities to see a variety of shorebirds and waterfowl along its beach and freshwater pond.

Are there any circular walks available?

Yes, many of the best hikes in the area are loops. For a moderately challenging circular route, consider the Prospect Hill – Brickyard Site loop from Chilmark, which covers diverse terrain. For a much shorter and easier loop, the Salt Pond Loop — Falmouth is a great option just across the sound.

What should I know about parking at the trailheads?

Parking can be limited, especially at popular spots during peak season. Preserves like Great Rock Bight are known for having very small parking areas that fill up quickly. It's always a good idea to arrive early in the day or consider visiting during the shoulder seasons (spring and fall) to secure a spot.

Are there any trails that lead to a good beach?

Many trails offer the rewarding experience of ending at a beach. The path at Cedar Tree Neck Sanctuary is well-regarded for its good beach access. Another excellent option is the Trunk River Beach loop from Woods Hole, which combines a pleasant walk with time on a beautiful stretch of sand.

What is the best time of year to hike in Dukes County?

While hiking is possible year-round, the best times are typically spring and fall. During these seasons, the weather is pleasant, the trails are less crowded than in the summer, and you can enjoy the changing foliage or spring wildflowers. Summer is also beautiful but be prepared for more people and insects.

Are there any particularly quiet or less-trafficked trails?

For a quieter experience, consider exploring some of the smaller preserves. The The Knob — Falmouth trail, while on the mainland, is a short, serene walk to a beautiful viewpoint. On the island, visiting popular spots like Menemsha Hills or Great Rock Bight on a weekday or outside of peak summer hours can also provide a more peaceful hike.

Most popular routes in Dukes County

Easy hikes in Dukes County

Most popular attractions in Dukes County

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Check out more Hikes throughout Dukes County below and find the perfect route in your destination.

Manuel F. Correllus State ForestOak BluffsVineyard Haven

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