Your Next Weekend Escape: Martha’s Vineyard

All summer through Labor Day weekend, the SeaStreak ferry makes a weekly round trip between Manhattan and Oak Bluffs, Martha’s Vineyard. You’ll touch down on island just after 9 p.m., so head straight to The Christopher. This 15-room boutique hotel is located right at the center of Edgartown, a minute’s walk from dozens of shops and restaurants. The vibe here is beachy-chic: Rooms are decorated in colorful printed wallpaper with pops of periwinkle blue, pink and coral, and there’s a cozy back terrace perfect for relaxing by the fire pit. By now, you’re probably feeling restless from the ferry ride, so stroll just down the street to The Port Hunter, a lively restaurant and bar with live music until midnight on Fridays.

Fuel up for the day at Behind the Bookstore where the sprawling outdoor patio is the perfect spot for coffee and breakfast. You’ll find everything from Belgian waffles to yogurt and granola bowls on the menu, but our go-to order is the fancy toast topped with house-cured beet salmon, cream cheese and dill. After breakfast, make your way to Wheel Happy and rent some bikes for the day. The entire island was basically built for cycling so you can follow the bike path from Edgartown to Katama, passing farmland, grazing cows and scenic bay views along the way until you’ve arrived at dune-swept South Beach.

For a picnic-style lunch on the beach, pack a handful of prepared salads, homemade kale pesto, cheeses and freshly baked bread from Morning Glory Farm. If you’d rather sit down, grab a table at the Right Fork Diner, located just across the way from South Beach at Katama Airfield. There, you can watch tiny biplanes take off and loop across the sky while digging into a lobster Cobb salad.

After a long day at the beach, spend the early evening window-shopping around the art galleries and boutiques that line Edgartown village. For dinner, it’s a ten-minute drive to Oak Bluffs where Crayola-colored houses surround a great lawn. Make a dinner reservation in advance for the Red Cat Kitchen, a small and quirky farm-to-table restaurant that’s packed almost every night. The menu changes constantly, but expect things like sea scallops over lobster risotto, melt-in-your-mouth fried chicken and the best balsamic Brussels sprouts we’ve ever tasted. If you have any room left after dinner, you’re in the right place: Oak Bluffs is home to Back Door Donuts, a speakeasy-style bakery, and Ben and Bills, easily the best ice cream on the island.

Get an early start and take the scenic drive up the island to the bucolic towns of Chilmark, Aquinnah and Menemsha. You’ll pass winding stone walls, rolling pastures full of sheep and horses, and narrow pathways leading toward the ocean. On the way, grab an island-famous bacon, egg and cheese on a homemade biscuit from 7a Foods. Then, continue to Aquinnah, the westernmost tip on the island, which is known for its vibrant red clay cliffs. You can snap photos from the overlook or walk the trail down to Moshup Beach. (Just be warned—this stretch of sand is notoriously clothing-optional.) Next, it’s a ten-minute drive to Menemsha Hills, a peaceful four-mile walking trail that loops through wildflower-speckled woodlands and leads to a gorgeous, secluded beach overlooking Vineyard Sound.

After all that exploring, you’ve probably worked up an appetite. Luckily, there’s one stop left before you have to catch the ferry. Just minutes from the hiking trail, you’ll find the sleepy seaside village of Menemsha, which is full of seafood shacks and fishing boats on the harbor. Make a beeline Menemsha Fish Market, which boasts one of the best lobster rolls on the island—served cold with mayo and celery, or warm and buttered on a toasted bun. We always go for the combo, which comes with a seriously rich cup of lobster bisque or clam chowder. From there, take the scenic route back to Oak Bluffs and sleep the whole boat ride home.