WHERE TO STAY
I’ve stayed in Martha’s Vineyard several times before and my favorite place to stay has been Aquinnah (formally Gay Head), hands down. It’s picturesque, peaceful, and serene, away from the bustling crowds and loads of traffic. The only downside is that you have to drive quite a distance to get to the other side of the island in order to visit places like Vineyard Haven, Oak Bluffs, and Edgartown.
WHERE TO EAT
Among the Flowers Café in Edgartown (we had lunch there, but I hear the breakfast is great too), The Bite in Menemsha, The Black Dog Bakery and Café on State Road in Vineyard Haven. Also I highly recommend the crab cake sandwich from Dreamcatcher, as well as the California rolls from Faith’s Seafood Shack & Sushi Bar, which are both in Aquinnah.
For a sweet treat – there are tons of places to get ice cream & frozen yogurt; however, by far the best place was Vineyard Scoops in Edgartown. Also in Edgartown is Scoop Shack, which has ice cream & frozen yogurt, as well as bags, bins and barrels of old-fashioned candy including saltwater taffy!
WHERE TO SHOP
Edgartown is absolutely adorable and by far my favorite place in Martha’s Vineyard for shopping – with its streets lined with charming boutiques, it’s the perfect place to window shop.
I also particularly loved Alley’s General Store in West Tisbury, which is a fun, whimsical old-fashioned general store, packed to the brim with sundries.
Vineyard Haven and Oak Bluffs (specifically Circuit Ave) have tons of stores to shop as well!
WHAT TO DO
Go to the beach
My favorite beach might be Lobsterville – it was definitely the dogs’ favorite! Also, Menemsha has a nice, small public beach that’s quite charming.
Visit festivals, flea and farmers markets
The Artisans Festivals located at Historic Grange Hall in West Tisbury all week from 10am-2pm
Featherstone Flea and Fine Arts Market on Tuesdays from 9:30am-2pm at Featherstone Center for the Arts in Oak Bluffs
Chilmark Flea Market on Wednesdays and Saturdays from 9am-2pm at 142 North Road in the field across from the old schoolhouse
The West Tisbury Farmers Market on Wednesdays and Saturdays from 9am-12pm at Grange Hall
Antique Show & Sale at Grange Hall on Fridays from 9am-3pm.
Oak Bluffs Open Market on Sundays from 10am-2pm at Washington Park in Oak Bluffs
Check the calendar for annual events
When we were visiting the Annual Book Sale at Oak Bluffs Library was taking place.
Tour the lighthouses
There are five lighthouses on the island – The West Chop, The East Chop, Edgartown, Gay Head, and Cape Poge
Admire the Aquinnah Cliffs
The spectacular view of these truly breathtaking Clay Cliffs is definitely worth a trip out to Aquinnah!
Visit the Oak Bluffs Campgrounds
A quaint neighborhood within Oak Bluffs consisting of over 300 colorful Carpenter Gothic Victorian cottages with wedding-cake trim, which were mainly built in the 1860s and 1870s. You can a few pictures of the cottages here!
Ride the Flying Horses Carousel
Located in Oak Bluffs, the Flying Horses Carousel is the oldest operating platform carousel in America and was built in 1876!
Walk around Menemsha
Menemsha is a charming fishing village with a historic harbor, a public beach, as well as a handful of unique shops and a few seafood shacks & restaurants.