We are just about to rent a house near East Chop and Oak Bluffs for a week in July. Any suggestions?
If you plan on taking a car on the ferry, make reservations now. But it may already be too late.
If you get tired of the crowds, the up-island areas to the south and west are beautiful, and you can even find deserted beaches out near Aquinnah.
Thanks @MaineLonghorn, the house we’re renting has a car ferry ticket, so we’re all set on that front!
We go every summer. The Black Dog is tourist-y, but I wouldn’t think of having breakfast anywhere else. It’s in Vineyard Haven right near the ferry. We love Beach Road for a special-ish dinner. It’s sister restaurant is State Road which is also excellent. Obama eats there every year when he’s on MV. The Net Result is great for lobster “in the rough.” Bunch of Grapes is a great book store in Vineyard Haven. South Beach is my favorite beach on the island and that’s in Edgartown. You have to see the sunset in Menemsha. It’s very special. Chappaquidick is a nice day trip and worth doing. I know I’ll think of more. You’ll love it.
We loved renting bikes and pedaling around the island. It was low key and covered more distance than walking.
@ams5796, thanks…I’m starting a list!
Clam chowder at The Black Dog in Vineyard Haven.
Yes, the Black Dog is more than just breakfast. They serve all three meals and the food is good. It’s an experience there. They have a store that sells all the Black Dog merchandise that is ubiquitous around the island. (and elsewhere) There’s a lot of traffic around the island in July (we go around the fourth) especially around dinnertime. In fact, start making dinner reservations soon if there’s somewhere you really want to go (Beach Road?). They take reservations about a month ahead. The traffic is bad and parking at the popular areas is tight so leave enough time. Because of the traffic we’ve opted to barbecue on a few of our evenings. The best market to get wonderful meat, fish, sides etc (in fact everything you need for a barbecue) is Edgartown Meat and Fish. It’s really great. There’s a couple of Stop&Shops on the island too. We end up there a lot. (always mobbed). There’s a great old timey movie theater in Vineyard Haven. Hopefully, you won’t get a rainy day, but just in case. Lots of biking around the island. My kids have gone on some beautiful bike rides. You can rent bikes by the week. In fact, a lot of folks use the bikes as their main mode of transportation around the island. Gorgeous! Kayaking is very popular too. Walking around Oak Bluffs at night is fun. It’s kind of funky, in a good way. Ice cream is a must at Mad Martha’s. There are a few of them around the island. Ride the carousel in Oak Bluffs and grab the brass ring for a free ride. Last year for the first time we did a day trip to Nantucket and we loved it. We went to Cisco Breweries and hung out there most of the day. Lots of food and music. We walked around Nantucket. Very fun experience. I’d recommend that if you feel that you have enough time. A great ice cream shop over there the is The Juice Bar. Also, in MV (Oak Bluffs) is this cool bakery that sells amazing donuts called Back Door Donuts. People line up every night around 7 pm to get these incredible donuts right out of the oven. They were huge. We won’t be doing that this year. haha The donuts are as big as your head. My kids were appalled. You might want to look into driving up island to Aquinnah to see the red clay beaches. (mentioned above) It’s quiet and breathtaking up there. We did it years ago. Now, my kids won’t budge for any “sightseeing”. You might see Larry David and other celebrities’ homes up there.
All great information, thank you. We’ve rented a house that is walking distance of Oak Bluffs center for a week in mid-July and we will have a car. We’re going with good friends and one or more of our adult kids may join us for part of the week. I think we’ll rent bikes as I’ve heard the bike path is great.
I second the suggestion to go to Nantucket for a day trip (there is an inter-island ferry in the summer). The two islands are different—Nantucket has just one “town” plus the village if Sconset, while the Vineyard has six. Plus, Nantucket is much less developed overall—no chain stores allowed, the entire island is in a historic district, strict zoning keeps structures mostly the same, and over 50% of land is permanent conservation land. The island has one of the largest collections of pre-Civil War architecture in the US. The year-round population if Nantucket is half that of the Vineyard, although in August, Nantucket, like the Vineyard, will be very crowded. Visit the Whaling Musem in Nantucket to learn about the island’s history as a whaling center. Great beaches and walking/bike paths all across the island. Taxis and a bus service take you anyplace you want to go.
The ice cream at the Juice Bar (mentioned upthread) is good, but in the summer the lines are very long and you can wait for as much as an hour. There is a great ice cream store at the Island Kitchen without the monumental waiting time.
People in the Nantucket camp love it—similarly those in the Vineyard camp are we equally as loyal. The Vineyard gets more celebrities visiting while Nantucket gets more CEO types.
For food I like the MV Chowder Co, the Offshore Ale Co, and Sharkys for Mexican lunch is good too. THere’s a famous donut shop (Backdoor maybe?) that seems to be a must-do but I’m not a donut person. Of course, there’s the Flying Horses, grab some fried clams from the window beside there to snack on 
South Beach is nice. Head to the sight of Jaws, jump off the bridge, walk through the campground/gingerbread house association area. Couple of dive bars if you’re into that, I think its fun to stop in and have a mid-afternoon cocktail. Personally I wouldn’t bother going to Nantucket, that should be a vacation in itself.
Another thing to note is the public transportation is great in the summer months. Its cheap, you can avoid the parking nightmares, and its a good way to see things…I would avoid scooters, everyone is a tourist and no one knows where they are going lol.
Plan to take a couple of hours walking around the Camp Grounds in Oak Bluffs (Wesleyan Grove, run by the Martha’s Vineyard Camp Meeting Association) – it’s right near the center of town, a few blocks from the town green. It’s a Methodist camp meeting location dating back to the early 19th Century, and it’s chock full of adorable, variegated gingerbread cottages dating from the 1860s forrward arranged cheek-by-jowl in rough circles around the central meeting area. Many of them are still used by Methodist clergy and their families. Sometimes there are cultural events in the Camp Grounds, too – music performances, lectures, sermons. In mid-August, when you won’t be there, there’s a night where everything gets decorated and lit up with paper laterns, but it’s fun to see any time.
The Camp Grounds were a hotbed of abolitionist activity in the 1840s-50s, one of the results of which was that Oak Bluffs became a national vacation spot for affluent free African-Americans. That continued throughout the 20th Century and into this one. It’s why Barrack Obama spent his summer vacations on the Vineyard. I don’t know if it’s still true, but 40 years ago Oak Bluffs was majority Black during July and August. And since it was the poorest of the three towns in the eastern half of the Vineyard, it was probably the only place in America where in general the White population was much less well off than the Black population. Oak Bluffs’ special status for the African-American elite is reflected in Dorothy West’s novel The Wedding and Spike Lee’s film The Ink Well.
@JHS, thanks for the background. I knew something about that history, but you’ve inspired me to explore further. I did spend a couple of days there with friends a few years ago and we stayed in a cottage in the Camp Grounds. I’m also familiar with the campground in Thousand Island Park in the Thousand Islands, NY, originally a similar Methodist camp ground.
If you’re there on Sunday try to get a brunch reservation at Lola’s. They’re open other times too.
We enjoyed our stop at Bad Martha’s Brewery in Edgartown. It is surrounded by a (plant) nursery and it has a nice outdoor patio area with cornhole and tables, etc. My name is actually Martha so we enjoyed getting some cool t-shirts and stuff - that said “Bad Martha”…pretty fun. It would be a great stop on a bike ride. We absolutely loved our day on MV - I’m super jealous!