Chilmark – Aquinnah Headlands Preserve loop from Katama Airpark
Chilmark – Aquinnah Headlands Preserve loop from Katama Airpark
2.5
(13)
43
riders
Chilmark – Aquinnah Headlands Preserve loop from Katama Airpark
03:12
67.8km
360m
Road cycling
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.
Last updated: April 27, 2026
Tips
The surface along some of this route may not be suitable
Some segments of your route comprise a surface that may not be suitable for your chosen sport.
After 12.9 km for 661 m
After 28.1 km for 192 m
After 54.3 km for 661 m
Waypoints
Start point
Bus stop
Get Directions
23.1 km
Chilmark
Highlight • Settlement
Tip by
28.2 km
Nashaquitsa a
Nature Reserve
31.4 km
Gay Head Community Baptist Church
Highlight • Religious Site
Tip by
33.6 km
Aquinnah Headlands Preserve
Highlight • Natural Monument
Tip by
34.9 km
Moshup Beach
Nature Reserve
52.0 km
Grey Barn Creamery
Highlight • Cafe
Tip by
52.8 km
West Tisbury
Highlight • Settlement
Tip by
53.2 km
Old Millpond
Lake
67.8 km
End point
Bus stop
Way Types & Surfaces
Way Types
32.0 km
17.8 km
16.4 km
929 m
680 m
< 100 m
Surfaces
39.0 km
27.0 km
1.63 km
245 m
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Elevation
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Weather
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Today
Sunday 12 July
27°C
16°C
0 %
Additional weather tips
Max wind speed: 17.0 km/h
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Description
The Chilmark – Aquinnah Headlands Preserve loop from Katama Airpark is one of Martha's Vineyard's most rewarding road cycling routes, offering a dramatic shift in scenery and terrain. This moderate 42.1-mile (67.8 km) ride, with 1169 feet (356 metres) of elevation gain, takes approximately 3 hours and 11 minutes to complete. It's an ideal choice for experienced road cyclists seeking a challenging tour of the island's diverse landscapes, from flat coastal paths to rugged, hilly terrain, making it a comprehensive Chilmark Aquinnah Headlands Preserve cycling route.
What to expect on Chilmark – Aquinnah Headlands Preserve loop from Katama Airpark
This route is a journey of contrasts. Starting from Katama Airpark, you'll begin on the flatter, more developed "down-island" roads, enjoying dedicated paved bike paths like the Katama Road path. As you head towards Chilmark and Aquinnah, the terrain transforms into the island's "up-island" section, characterized by rolling glacial hills and constant climbs and descents. You'll cycle through Chilmark's picturesque pastoral farmland, past stone walls and wildflower meadows, with views towards Tisbury Great Pond. The highlight is the Aquinnah Headlands Preserve, where you'll encounter the dramatic, multi-colored Gay Head Cliffs, offering incredible viewpoints of Vineyard Sound and the Atlantic Ocean. Be prepared for a challenging ride in the up-island areas, as many roads are narrow, shared with cars, and often lack dedicated bike lanes, requiring good fitness and caution.
Planning your visit
Parking is available at Katama Airpark, which serves as a convenient starting point for this loop. Given the narrow, shared roads in the Chilmark and Aquinnah sections, especially during peak traffic season, it's advisable to start early in the day to minimize encounters with vehicles. There are no specific permits or fees mentioned for cycling this route. Always carry sufficient water, particularly during warmer months, as shade can be limited on some stretches of the up-island roads.
Trail details
- Distance: 42.1 miles (67.8 km)
- Elevation gain: 1169 feet (356 metres)
- Difficulty: moderate
- Estimated time: 3 hours and 11 minutes
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