Travel Diary: A Guide to the Up-Island Towns of Martha's Vineyard, MA
Welcome to part one of a three-post series on visiting Martha’s Vineyard, MA.
Today’s post dives into the Up-Island towns of Chilmark and Aquinnah, with tips on the best beaches, restaurants and places to stay.
Let’s dive in!
Aquinnah
Mostly dry: Alcohol sold only in restaurants with more than 15 tables, of which there are approximately two.
Dress code: By day, cutoffs and a bathing suit, or literally nothing at all*, by night, summer dresses and linen.
Aquinnah is home to the Wampanoag tribe’s lands, and indeed some of the prettiest spots on the island. When European colonists arrived and the town was pared off from neighboring Chilmark, the town fathers decided to name this lovely slice of island Gay Head (I know, I know, I will wait here while you snicker) for its lovely multicolored sand-dune cliffs. It stayed named that way until 1997, probably because of someone’s peculiar sense of humor, and then the authorities changed it to the very PR-friendly Aquinnah, which is Wampanoag for “land under the hill.”
You can enjoy the very best views of these painted cliffs from the beach and trails at Moshup, but caveat amigo, for this year while walking, thankfully alone and not with any kiddos, I discovered that there is *a very nude beach (not strictly legal) if you head west towards the cliffs from the entrance to Moshup Beach. It’s a beautiful walk, but know that you will get an eyeful of… social awkwardness along with the dunes, tide pools, dramatic Ice Age boulders, hovering magnificent birds of prey and other terribly charming local whatnot.
If you can afford it, spend a night or two at The Outermost Inn, which is one of the most magical places in the world. Set at the top of a hill on several acres of the most magnificent landscape I’ve ever seen, this inn and bar/restaurant is a place of magic and enchantment. It’s very expensive and very beautiful and very relaxing. When you enter the lobby, you will see a view straight out the back porch’s glass French doors to the star of the show, Aquinnah’s grassy rolling hills, gnarled trees, and the sea. If you’re lucky there will be a herd of deer grazing and a majestic osprey in the enormous nest. (There is a telescope in the lobby trained on the nest so you can check on them throughout the evening on your way to and from the loos.)
The thing to do is to make an advance reservation (I call in August for May) for a time about an hour before sunset on the evening you wish to visit. Then dress up in your dreamiest clothes and sensible shoes (think grass and gravel outside) and show up about an hour before that for cocktails at the bar, which is positioned facing out towards this breathtaking vista. The best seats are the Adirondack chairs, the small individual tables on the patio, and the seats that look across the bar, from which you can gaze and congratulate yourself on the many blessings in your life which have led you to this perfect moment. Then go inside, and stuff yourself on local seafood, house-made pasta, wines, cocktails, coffee and divine desserts while you watch the sunset from on high. Triumphantly have someone else drive you home, or book a room and never ever leave.
Truthfully, this stunning town is as wild and remote as the Vineyard gets. I am in love with it, and when I finally make it big I am going to buy a house by the water here, and make jam from my blueberries.
Chilmark (and Menemsha)
Bone-dry: The last fully dry town on the Vineyard.
Dress code: Whatever people wear to go fishing. Wellies. Plastic bibs with lobsters on them. Sporty sunglasses for sportsmen.
Chilmark is large, rural and expensive. In fact, Wikipedia tells me Chilmark had the highest median home sale price of any town or city in Massachusetts in the year 2013, so wow. It includes the appropriately uninhabited island of Nomans Land, as well as the charming fishing village of Menemsha. Most of the township is rural, a fairly exclusive maze of private lanes, punctuated by scenic salt-ponds, and makes a marvelous location for home rental, or better yet, ownership. However in tiny Menemsha Village you will find a modest number of accessible things to do as a visitor to the town.
For starters there is a small public beach with parking, suitable for little ones as well as bigger kids. There’s a pier for the fishermen, of which there are many, and near the beach end some kind soul fills a sort of alfresco touch-tank with crabs and snails and other things from the shallow waters of the pond and harbor for the curious to marvel over. At the end of the day, the critters go back in the water, and we’ve been lucky enough to be asked to help repatriate them, to the great delight of the participants, as we said goodbye and thank you to each one as we tossed it back into the lapping waves as the sun melted into the horizon. Amazing.
If you’re hungry, there are two options:
Larsen’s Fish Market, of the jaunty blue sign, is a great place to pick up either uncooked or prepared/cooked seafood and fish including crabcakes and chowders. This is just a market, though, so there is no formal seating, however you can take your cooked food outside to eat on the pier, or down on the beach, if you don’t want to eat back at your accommodations.
Just up the road from the marina is the Home Port Restaurant. Not only do they offer both inside and outside seating, but they will bring you buckets, mixers and ice for your drinks, which you’ll have brought with you because this town is BYOB! It is more expensive than Larsen’s and boasts casual picnic tables, lots of stuffed trophy-fish, and a mini-canoe filled with ice and oysters, shucked for you on the go on busy summer nights. Definitely make a reservation in advance, and try to plan dinner to coincide with the sunset so you can enjoy the beauty of the changing sky reflected in the pond while you eat. The food here is pretty simple, and isn’t going to win any James Beard awards. It is definitely not the island’s best chowdah, but the fried oysters, raw shellfish, stuffed lobster and crab cakes are all plenty good and the views make for magic seasoning. Home Port also has a takeaway order window, called The Back Door, where you can get your lobster roll and fried clams to go, if you’re feeling a bit restless.
If you’ve never been to the Vineyard, I hope this guide will be a great start for your exploration of the island. If you’re a Vineyard lifer, please post away in the comments and let me know about your favorite spots, so I can try them when we return in 2021!
TIPS
For more recommendations by town, please check out our Down-Island Martha’s Vineyard Travel Diary post.
If you’re a Martha’s Vineyard rookie, please make sure to visit our Newbie’s Guide for tips to make your first visit the start of a memorable vacation tradition.
For deep discounts on beach access and parking, become a member of the Trustees of the Reservation and enjoy the righteous pride of supporting amazing places all over Massachusetts.
It’s not to early to start planning a visit to the Vineyard for next summer. If you’re planning a trip, here are some of my very best packing tips.
If you like my travel diaries for Martha’s Vineyard please pop over and have a look at the one for Dublin, Ireland!
