I (Chrissie) spent the summer after my freshman year of college living with eight friends on Martha’s Vineyard, where I painted houses and waitressed. So I was excited to return to the Vineyard for the first time in decades for a family summer vacation.
We have traveled a lot as a family, but we had never rented a home and stayed in one location for a week, so this was new to us! We had also never done a trip that included our kids’ partners, nor done a vacation in which many of us were working remotely while there. We planned the trip based upon attending an East Coast wedding, and thus we landed on Martha’s Vineyard as the perfect spot, given that it offered beach and town experiences, and everyone could explore separately or together, depending on work schedules.
Our weeklong trip included 8 of us: my husband and I, our three kids in their mid-late 20s, and their significant others. The Vineyard had undergone some changes in the decades since I’d lived there (like elsewhere, higher prices and more traffic!), but the island retains its charm and beauty and is a beautiful getaway location that offers relaxation as well as activities.
Many of our group were working remotely during our visit, so we often spent the mornings grabbing coffee at one of the charming coffeeshops in town and then exercising, exploring, or working. Afternoons were spent at the beach, exploring all the various gems the island has to offer, or visiting with friends who spend the summer on the Vineyard, followed by dinner based on wherever we happened to be exploring that day. Among our many great experiences, some of my favorite memories are of lazy beach time at State Beach, exploring the beauty of small towns on the island, and enjoying a picnic dinner of fresh lobster rolls on the beach at sunset in the small fishing village of Menemsha.
Here is our FabList of where to stay, what to do, and where to eat on Martha’s Vineyard.
About Martha’s Vineyard:
Martha’s Vineyard is an island in Massachusetts located off the coast of Cape Cod. It is just under 100 square miles in size and is approximately 20 miles long. There are about 23,000 residents who live on the island year-round, but during the summer season, the number of people balloons to nearly 200,000! There are no fast food chains or large chain stores on the island; rather, it has smaller local boutiques and shops, a few grocery stores, and a variety of farm stands and restaurants.
How to Get There:
You can fly to the island or take a ferry from Cape Cod. We flew into Logan/Boston, spent a couple of nights with friends on Cape Cod, and then took the car ferry from Woods Hole (car ferries go to either Vineyard Haven or Oak Bluffs). If you plan to take a car over, YOU MUST BOOK YOUR CAR FERRY REALLY EARLY! I booked our car ferry tickets about 6 months in advance and couldn’t get tickets for the days we were arriving/departing. It took six months of slow progress on waitlists until I finally secured reservations on the right days/times. You can also rent a car on the island, but I heard prices are steep (I didn’t check personally).
Where to Stay:
Island locations are often broken out by ‘Down Island’ and ‘Up Island’.
‘Down Island’ includes Edgartown, Oak Bluffs (OB), and Vineyard Haven, and offers lots of housing options. These are larger towns with shopping, restaurants, public beaches, and other amenities.
‘Up Island’, which includes Chilmark, West Tisbury, Menemsha, and Aquinnah, is much more rural and has very few shops and restaurants. This beautiful part of the island abounds with quiet and tranquility.
There are homes and hotel options, and you can rent via a company or via Airbnb, etc. Prices, of course, vary a lot. A home for the week can run from roughly $6k – $20+, depending on location, water access, number of bedrooms, etc. You can choose to stay in a town, on a farm, in the woods, on the beach, in a small fishing village, and more – it depends on what vibe you’re looking for and what your budget is. Initially, we were going to stay near a beach, but ended up renting a house in Edgartown, a couple of blocks from downtown, which made it easy for everyone to walk to coffee, restaurants, shopping, a small local beach, etc. We then drove or biked to places outside of Edgartown. We rented via Point B Realty.
Transportation:
The eight of us rented two cars (in Boston) to get around the Island. We also rented bikes (from Edgartown Bicycles, which gave a discount for renting ahead of time). We stayed in Edgartown, and it seems that most everything was within a 30-minute drive from us.
Places to Visit:
Edgartown:
Edgartown, an old whaling village, is a beautiful town on the water that’s filled with traditional Cape Cod shingled homes and hydrangea bushes. Walking around, you feel you are in a movie set, or an Erin Hildebrand beach-read book. If you know what Vineyard Vines clothing style is, then you have an idea of what Edgartown is like – casual, preppy, and well-manicured. The town has lots of restaurants, coffee shops, ice cream shops, boutiques, bars, etc. Traffic is bad coming into town, however, and some of our friends who live elsewhere on the island refuse to enter Edgartown from June to August due to the traffic/crowds. We used Edgartown as our home base; however, and it was great for our group to have the flexibility to walk to coffee, meals, ice cream, etc., as well as to bike to the beach. There is also a smaller local beach within walking distance.
Oak Bluffs:
Settled in the 1600s, Oak Bluffs, or OB, is more casual and laid-back than Edgartown, offering more nightlife and a relaxed vibe. Whereas Edgartown has beautiful white clapboard homes and green lawns, Oak Bluffs is known for its ‘Gingerbread Houses’. There are over 300 of these colorfully painted historical homes (similar vibe to the ‘painted ladies’ Victorian homes in San Francisco) that help create the town’s colorful, bohemian atmosphere. OB also houses the country’s first carousel and has a large green space with a bandstand in the center. The town also has beach swimming.
Vineyard Haven:
Vineyard Haven is smaller than Edgartown, also has many Cape Cod-style homes, and offers boutique shopping, ice creameries, bakeries, and lots of dining options. It’s a bit more spread out than Edgartown and not as much of a town to ‘wander for the day’ as Edgartown is.
Menemsha:
Menemsha was one of our favorite places on the island. It’s an old fishing village that remains active to this day. It’s tiny and charming, with boats in the harbor and a great little beach where you can have a sunset picnic dinner of a fresh lobster roll or chowder from one of the local eateries with fresh-caught offerings.
Chappaquiddick:
Chappy is the small ‘island’ just off Edgartown, which is reached by a 90-second ferry from Edgartown. Chappy has homes on it, as well as one tiny general store, a Japanese-style garden that boasts local fauna, a nature preserve, and that’s about it. Known for the Kennedy incident on a bridge, it’s a nice place to do a bike ride (there’s one ‘loop’ road on the island, about a quarter of which is sandy).
Beaches/Swimming:
There are many beaches all around the island, but the ones we went to were:
South Beach/Katama:
This large public beach, with waves, is a 20-minute bike ride from Edgartown. It has public toilets and parking.
State Beach:
Located on the sound, State Beach is calm and excellent for swimming. It’s a 10-minute bike ride from Edgartown. There is street parking, which can get crowded on a sunny summer day. It’s a great place to hang out with an umbrella, a beach chair, and a book. It has lifeguards, but no public toilets.
Fuller Street Beach in Edgartown:
This small beach is within walking distance of downtown Edgartown. When we were there, it had more seaweed than State Beach, so it wasn’t as good of a swim spot.
Menemsha Beach:
Menemsha Beach is calm and suitable for swimming. It gets sunset views and is a great place for a picnic dinner.
Lambert’s Cove:
This is a beautiful beach, but you must be a resident/have a pass to get on it. If you’re staying nearby, be sure to check if your rental comes with a pass to it.
Ponds:
Around the island, there are some freshwater ponds (more like small lakes) that are available for public swimming. You can search to see if they are near your location.
Running/Biking/Fishing/Farm Visits:
Running near Edgartown:
There are good running trails in the Manuel F. Correllus State Forest (5,300-acre forest in the middle of the island), as well as in the 150-acre Caroline Tuthil Preserve. Beware of ticks, though, as they are a REAL THING in the Vineyard, and check thoroughly after being on the trails…or anywhere really!
Biking:
There is great biking all over the island. Search based upon your level and location.
Fishing/Boating:
We didn’t fish or participate in boat activities, so I can’t comment on this, except to say it’s available for those interested. Winds Up in Vineyard Haven offers a variety of rentals, including kayaks, SUPs, and small sailboats.
Farm Visits:
Martha’s Vineyard has a LOT of farms, which include farm stands with fresh produce, like Morning Glory Farm and the Grey Barn. If this is of interest, please search further online to find those in your area.
Shopping:
Most of the fashion shopping on the island is very high-end, and this was not a focus of our trip, outside of window shopping while wandering, so I can’t recommend specific spots. Also, it seems that every shop, from coffee shops to boutiques, on the Island offers branded Martha’s Vineyard branded merch such as sweatshirts, tees, and more. There is NO problem finding nice branded Martha’s Vineyard items!
Groceries:
Morning Glory Farms near Edgartown is a wonderful place for fresh produce, bread, and more. There are other “General Stores’ throughout the island that offer high-end salads and produce as well. For general groceries, there is a Stop and Shop grocery store in Edgartown and Vineyard Haven.
Dining:
There are lots of restaurants everywhere on the island. They are all expensive, given it’s a vacation spot, and many ingredients need to arrive by ferry. Below is a list of restaurants we went to (those have an * by the name), as well as those that were recommended to us by friends who have homes on the island, that we did not have a chance to visit. Most places require reservations.
Edgartown:
*Behind the Bookstore (coffee shop/breakfast/lunch spot that has a nice, casual vibe and a good outdoor, covered dining area)
*Espresso Love (coffee shop/breakfast/lunch spot tucked away a bit with nice garden seating)
*Rosewater Market (coffee shop/breakfast/lunch spot with a nice gift shop and front patio seating area)
*Seafood Shanty (outdoor dining on the water)
*The Newes From America (pub in town)
*Edgartown Pizza (we did take out)
*Among the Flowers (breakfast/lunch spot)
Backyard Taco (small, casual)
Harbor View (lovely fancy hotel/fancy dinner)
The Quarterdeck (casual grab-and-go spot on the harbor for a good fish sandwich)
The Wharf (burgers, music, cocktails)
Alchemy (dinner)
19 Raw (nice oyster bar/dinner)
Oak Bluffs:
*Nomans (no reservations, fun casual spot with outdoor dining/music/cornhole located near State Beach, just outside of town)
*Lookout Tavern (popular casual spot for dinner and beer that looks out over the water. No reservations, and can be a wait, but you can explore the town or have a drink while you wait.)
*Nancy’s (lunch and dinner spot on the water with a vibe and good blended drinks).
Vineyard Haven:
*Carboat Coffee (in a small strip mall, coffee, pastries, Lebanese food. Take to the beach for a picnic.)
Garde East (lunch, dinner, and ‘doctails’ on the water).
Beach Road (nice dinner spot, owned by the same owners as State Road restaurant in West Tisbury)
West Tisbury:
State Road Restaurant (Tuesday is burger night)
Menemsha:
*Larsen’s Fish Market (pick up lobster rolls to eat on the beach at sunset!)
The Homeport (seafood and oyster bar)
Aquinnah/Gay Head:
Outermost Inn (beautiful drive to the end of the island. Have a drink at sunset in Adirondack chairs)
