Chilmark, a region in Dukes County, Massachusetts, is located on Martha's Vineyard and offers a rural landscape for outdoor activities. The area features preserved farmland, rolling hills, and a tranquil environment, shaped by glacial activity into a diverse terrain of low wetlands, woodland groves, coastal plains, and rocky shorelines. This geography provides varied settings for several sports like hiking, road cycling, jogging, touring cycling, and more, with access to both Vineyard Sound and the Atlantic Ocean.
91
Routes
4.7
(69)
Average rating
787
People visited

4.7
(18)
143
hikers
10.4km
02:51
160m
160m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

4.5
(8)
24
hikers
6.09km
01:41
100m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

4.8
(5)
18
hikers
7.88km
02:07
100m
100m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

5.0
(2)
15
hikers
6.92km
01:54
120m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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5.0
(4)
60
riders
62.3km
04:23
740m
730m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
8
riders
39.1km
02:54
440m
440m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

6
riders
41.2km
02:59
550m
550m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3
riders
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.0
(1)
35
riders
71.3km
03:26
700m
700m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

28
riders
41.5km
01:53
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

19
riders
23.7km
01:13
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

4.5
(2)
16
riders
50.7km
02:34
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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10
riders
60.5km
03:41
440m
440m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
11
riders
43.8km
02:48
470m
470m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5
riders
31.6km
01:58
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
5
riders
21.5km
01:22
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.0
(2)
4
riders
44.6km
03:27
530m
530m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

5.0
(3)
4
riders
43.1km
03:49
760m
760m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

3
riders
21.7km
01:53
330m
320m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

3
riders
43.2km
03:22
490m
490m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
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10
runners
14.3km
01:36
220m
220m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

8
runners
6.21km
00:39
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
9
runners
7.57km
00:48
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

7
runners
10.8km
01:09
150m
150m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Chilmark, located on Martha's Vineyard, offers a rural landscape for outdoor activities. The region supports hiking, road cycling, jogging, touring cycling, mountain biking, and gravel biking. It features preserved farmland, rolling hills, and coastal areas.
Chilmark features several notable hiking areas. Menemsha Hills Reservation offers trails with views of Vineyard Sound and the Elizabeth Islands. Waskosim's Rock Reservation provides views from its summit, and Peaked Hill Reservation offers vistas over the Atlantic and Squibnocket Pond. More information is available in the Hiking around Chilmark guide.
Yes, Chilmark offers trails suitable for various skill levels. The Island Folk Pottery Sculpture Trail provides a family-friendly art path through the woods. For more options, consult the Easy hikes around Chilmark guide.
Chilmark provides diverse cycling opportunities, including road cycling, touring cycling, mountain biking, and gravel biking. Routes traverse scenic areas, the historic town center, and island high points. Guides like Road Cycling Routes around Chilmark and MTB Trails around Chilmark offer specific routes.
Chilmark's landscape includes low wetlands, woodland groves, coastal plains, and rocky shorelines. Notable features include the sea stack at Lucy Vincent Beach and large tide-worn boulders. The fishing village of Menemsha is known for its west-facing views.
Chilmark features 12 routes across various sports on komoot. These routes have been rated by more than 550 users, achieving an average rating of 4.7 out of 5 stars. Over 4,800 visitors have explored these routes.
Komoot offers several guides for Chilmark, including Hiking around Chilmark, Road Cycling Routes around Chilmark, and MTB Trails around Chilmark. Other guides cover easy hikes, running trails, cycling, and gravel biking.
Chilmark offers several routes suitable for jogging and running. The Running Trails around Chilmark guide provides detailed information on available routes. These trails often traverse scenic areas of the region.
The Chilmark Town Offices can be reached by phone at 508-645-2100, ext. 2125. Their hours of operation are Monday through Friday, 9 AM to 5 PM. The official website for the Town of Chilmark is chilmarkma.gov.
Yes, Chilmark is home to several preserves. Menemsha Hills Reservation features 3 miles (4.8 km) of trails leading to a rocky ocean edge. Waskosim's Rock Reservation offers views from its summit, and Chilmark Pond Preserve provides views of Chilmark Lower Pond and the Atlantic Ocean.
Chilmark's terrain was shaped by glacial activity, resulting in a diverse environment. It features low wetlands, woodland groves, coastal plains, and rocky shorelines. The area includes rolling hills and high-elevation overlooks, offering varied conditions for different activities.

