Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Road cycling routes
United States
Massachusetts
Dukes County
Vineyard Haven

Vineyard Haven Harbor – Aquinnah Headlands Preserve loop from Vineyard Haven

Routes
Road cycling routes
United States
Massachusetts
Dukes County
Vineyard Haven

Vineyard Haven Harbor – Aquinnah Headlands Preserve loop from Vineyard Haven

Moderate

2.5

(16)

92

riders

Vineyard Haven Harbor – Aquinnah Headlands Preserve loop from Vineyard Haven

02:53

62.3km

420m

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: March 21, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 25.4 km for 192 m

Waypoints

A

Start point

Bus stop

Get Directions

1

24 m

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

25.5 km

Nashaquitsa a

Nature Reserve

3

32.4 km

Aquinnah Headlands Preserve

Highlight • Natural Monument

Aquinnah Headlands Preserve is a beautiful stretch of coastline on the northwestern corner of Martha's Vineyard. The colorful Gay Head Cliffs run along its length, overlooked by Gay Head Cliffs. …

Tip by

33.6 km

Moshup Beach

Nature Reserve

5

43.5 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

B

62.3 km

End point

Bus stop

Loading

Way Types & Surfaces

Way Types

47.7 km

14.3 km

301 m

< 100 m

< 100 m

Surfaces

42.2 km

19.6 km

320 m

227 m

Sign up to see more specific route details

Sign up for free

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)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Today

Thursday 21 May

17°C

8°C

68 %

Additional weather tips

Max wind speed: 22.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Nearby routes

Moderate

3.0

92

Road ride to Aquinnah Headlands Preserve – South Head

03:34h

79.3km

370m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy