The Best Town On Martha’s Vineyard

You are on the verge of taking the plunge and booking your Martha’s Vineyard vacation (of course booking your Martha’s Vineyard Hotel via the Martha’s Vineyard Lodging Association because then you book direct with the property and avoid commissions and surprise OTA fees!) but a pesky  question is nagging at the back of your head – “Holy Back Door Donuts, how do I know which is the best town on Martha’s Vineyard?”
Yep we’ve got six of the suckers, each with its own character and fans.

In no particular order here’s a quick overview to help you narrow down your choice:

Vineyard Haven (aka Tisbury)
One town, one Zip code but two names? Seems rather greedy and a tad confusing. Not unlike calling an island a “Vineyard” when it has no vineyards! Anyway, I digress. Simplest is to call it Vineyard Haven unless you want to track down a town official and trust me you don’t.
This is the year-round town, very locals focused and home to the Martha’s Vineyard Museum and the original Black Dog Tavern. Most stores and restaurants are open year-round and the ferry comes into Vineyard Haven throughout the year. Award winning restaurants (Garde East, Beach Road, Artcliff Diner) and stores (Green Room, Rainy Day, CB Stark, Leroux, Conrado) are located here and every August the town is host to the Beach Road Weekend 3 day music festival. Golfers can pass the day at Mink Meadows Golf Club or, if you prefer windmills on your fairway, at the Cove Mini Golf.
Definitely the most laid-back of the three “Down-Island” towns and quietest at night.
Oh yes and definitely NOT a dry town! Any alcohol you like is on offer, you just need to order some food to go with it (normally a good idea in my experience).

Oak Bluffs
Fun central. Home to the bright and beautiful Gingerbread Houses around the Tabernacle and also the famous Flying Horses Carousel. Lots of small bars and restaurants located around the marina, perfect for people and boat watching. The stores here lean more toward the touristy with T-Shirts and souvenirs in abundance but also with some more up-market stores like Stefanie Wolf Jewelry. This is definitely the place to come for late night activities with music nightly at The Ritz bar and through the summer at The Loft. Most summer afternoons music will also be heard outdoors at Nomans or the Tabernacle. This is the town with the most easily reached public beach.
August the town is packed with people coming for the African-American Film Festival or to be here for the Oak Bluffs Fireworks or for Illumination Night. Golfers head to spectacular Farm Neck Golf Club.
Seasonal ferries from many locations (Woods Hole, Hyannis, New Bedford, Manhattan, Nantucket, Rhode Island) make this the most accessible town in the summer.
Most restaurants, with the exception of Offshore Ale Company (making the best beer on the island by the way), Dos Mas and Sweet Life Café, are closed for the off season.

Edgartown
This is the prettiest of the towns and has a quintessential New England Main Street. Perfectly manicured streets with beautiful houses boasting pristine gardens. It’s fun just to meander the streets of Edgartown and admire the summer houses. It’s the town with the most hotel beds on the island, so is very vibrant in the summer. Some great shopping opportunities on and around Main Street (Nell, Slate, The Great Put-On) and some excellent seasonal restaurants (Détente, Alchemy, The Terrace, 19 Raw, Port Hunter). A very picturesque harbor with some rather impressive “yachts” moored there during the summer. Edgartown is the location of the car ferry across to Chappaquiddick (Chappy) which is always a worthwhile excursion to see Mytoi Gardens or visit East Beach or Wasque Preserve. Live music can be heard late at The Port Hunter in the summer. The town is very quiet in the off season and most restaurants, with the exception of Alchemy, The Wharf and Rockfish, are closed.

Chilmark
This is a very rural town with bucolic scenery to enjoy at every turn (Middle Road is particularly beautiful) and lovely beaches, some of which (eg. Lucy Vincent) are only accessible in summer to those staying in Chilmark . There isn’t really a town center and restaurants are not in large supply as this is the last dry town on the island. Chilmark Tavern is open in the summer and provides great food but you need to bring your own booze with you.
Menemsha fishing village is in Chilmark and is a popular destination to watch sunset. This is where you’ll find Larsen’s Fish Market (seasonal) and the Menemsha Fish Market (open year-round).
There are many farms at this end of the island and some have well stocked Farm Stands for you to visit. North Tabor Farm, Mermaid Farm and Grey Barn Farm (try their cheese!) are some of our favorites.
Not many hotel options other than the Beach Plum Inn & Menemsha Inn. It’s recommended to have a car to get around if staying “up-island” in Chilmark.

West Tisbury
Another town that has a distinct rural feel. It does have a town center which hosts both the Vineyard Artisans’ Fair and the Farmers’ Market throughout the summer and is home to the famous Alley’s General Store. No real shopping opportunities unless you’re after some great art from the Granary Art Gallery or the Field Gallery. State Road restaurant is open year-round.
The town is host to the annual Agricultural Fair and the Martha’s Vineyard Film Festival.
A glorious public beach at Long Point and some wonderful hiking choices (Cedar Tree Neck, Duarte’s Pond & Blackwater Pond) provide great outdoor activities. Lambert’s Cove Beach is a wonderful spot for sunsets. If staying here, at Lambert’s Cove Inn, you will need a car to get around to the other towns.

Aquinnah
The town is the furthest to the west and fairly remote. It is home to the Gay Head Lighthouse and the colorful Gay Head cliffs. Aquinnah has strong Wampanoag history and traditions. The landscape here is breathtaking with incredible views across to the Elizabeth Islands. There are some touristy stores at the cliffs but these are closed in the off season. It’s always worth stopping for pizza or goodies at the Orange Peel Bakery and dinner at the Outermost Inn is a wonderful experience for any Martha’s Vineyard trip. The town has lovely public beaches at Moshup and Lobsterville.
This is the quietest town on the island and nothing is open in the off season.

Safe travels,
Simon