The western part of Martha’s Vineyard, or “up-island” as it is known locally, is the least populated and quieter one, perfect for a relaxing getaway. Coming here off-season offers extra perks for nature lovers with unrestricted beach access and uncrowded trails. Worth noting that unlike other islands like Nantucket, many of the beaches on Martha’s Vineyard are private and open only to homeowners or cottage renters during the summer months. While it might be a bit too cold for a dip, visiting outside of the summer months means having the chance to experience and enjoy the private beaches all to yourself.
Lucy Vincent Beach
Arguably the island’s prettiest beach, Lucy Vincent Beach is an exclusive stretch of sand that requires a Chilmark resident vehicle sticker or town-issued walk-on pass ($$) during summer (June 1st – September 15th). Off-season, the path is all clear and anyone can venture out to the iconic Atlantic shoreline.
Take a long stroll on the wide, cliff-backed beach devoid of sun worshippers this time of year.
Head east towards the colorful cliffs where the beach narrows, creating slightly more private alcoves which typically fill with nude sunbathers during summer. The rust-colored rock formations really add to the stunning landscape and make for a good perch to take it all in.
Even the pond that lines the beach behind you showcases the beauty of “bucolic up-island”.
Aquinnah
The island’s westernmost tip, Aquinnah, is a must-see, combining splendid vistas and a fantastic walk on the beach. Park at the Moshup Beach parking lot and walk down the Moshup Trail through coastal scrubland to reach the beach.
Moshup Beach, also known as Aquinnah Public Beach, is yet another gorgeous beach perfect for a day stroll.
Tucked away underneath dramatic cliffs that keep on rising as you walk further north, this is the most secluded beach on the island. You can walk over a mile along the fine, sandy shoreline, looking for interesting shells and washed up driftwood with the lively surf as your only companion.
Marvel at the colorful sandstone and clay cliffs, owned by the Aquinnah Wampanoag Tribe, now under special environmental protection to prevent erosion. A designated national landmark, they rise 150 feet above the shore in a kaleidoscope of orange, brick red, purple and mustard yellow swirls formed 100 million years ago by glaciers. They change color and intensity as the day progresses and are simply marvelous come sunset.
The beach ends at the foot of Gay Head, the highest point of the cliffs which is topped by a lighthouse.
Retrace your steps to get back to the Moshup Trail and up to check out the Gay Head Lighthouse.
The views over the cliffs with the lighthouse in the distance are reason enough to come all the way here. The lighthouse itself is only open in the summer months at sunset so off-season it can only be a model in your seascape postcard photos.
Menemsha
Next head to Menemsha, a picturesque working fishing village that may seem familiar – it was the location of the movie Jaws!
Weathered boathouses line the harbor all the way to the beach with a few dirt roads crisscrossing the area ripe for exploration, which is pretty much the only thing to do in this sleepy little village. Watching the setting sun from the harbor here is a ritual with people applauding the sun for its day’s work the moment it slips below the horizon.
There are a few tiny shacks serving food and nothing beats a fresh lobster roll from Menemsha Fish Market eaten straight on the dock.
Great Rock Bright Preserve
The smallish but impressively diverse Great Rock Bright Preserve, less than 10 min from Menemsha, is great for fitting in a short hike and some more beach time.
A 1.2 miles trail crosses lovely woodland before bringing you down to the beach. The namesake rock can be seen fairly soon from an overlook atop a coastal cliff, sitting pretty in the middle of a cove just offshore.
It’s only a narrow strand of sandy shore, perfect for a slow walk looking for treasures brought in by the waves and rocks of every imaginable colors.
Horseshoe crab shells are a common find.
Menemsha Hills Reservation
For a more scenic and longer hike, go to Menemsha Hills Reservation which is famous for its vistas.
A 3.7 miles trail takes you up to Prospect Hill, the second highest point on Martha’s Vineyard at 308 feet, before descending to a rocky beach.
The Great Sand Bank overlook makes the climb back up after your beach stroll worth it, with 360-degree views and the nicest panorama of Vineyard Sound.
It’s time to make it back to Menemsha for the sunset or even Aquinnah if you want to see the cliffs bathed in even more colors.
