Martha's Vineyard, Massachusetts | Island Day Trip
If only a day at Martha’s Vineyard were endless …
Morning: Your journey begins on a boat. Catch the 9:30 a.m. Steamship Authority ferry out of Woods Hole. Across Vineyard Sound you’ll go for a 45-minute ride on open water and under a full sun to Oak Bluffs. When you arrive, bypass the downtown for a short moment and swing a left onto the appropriately named Seaview Avenue. On one side there’s the Atlantic; on the other, the equally magnificent Ocean Park and the homes of Gingerbread Square, which pay, in grand, lush style, artistic homage to the almighty shingle. From here, head a few blocks in-town for a little pre-lunch calorie splurge on a doughnut or apple fritter at M. V. Gourmet Cafe & Bakery–then walk off some of that treat with a jaunt down nearby Circuit Avenue, the town’s shopping center. (Chocolate! Dog treats! Clothing!)
Your real destination is something more whimsical: the Flying Horses Carousel, a National Historic Landmark and the oldest operating merry-go-round in the country. For the princely sum of $2 you can feel like a kid again, or watch actual kids try to grab the coveted brass ring. Keep peeling back those years by renting a Jeep at Adventure Rentals; then hop back on Seaview Avenue, toward Edgartown. Packed with views of the ocean and some of the island’s most beloved ponds, this six-mile trek is a favorite among drivers and cyclists. If the moment grabs you, park at Joseph A. Syliva State Beach (called locally simply “State Beach”), put on your bathing suit, and make the short jump into the water from “Jaws Bridge.” On a hot summer day you won’t be alone.
AFTERNOON: Edgartown is for strolling. Settled in 1642, this eastern-shore town packs an upscale, Old World feel. Head down North Water Street, a tight two-lane road marked by gracious homes and multimillion-dollar views. Dream a bit about a stay at the grand Harbor View Hotel; then follow the beachside path just across the road. The walk cuts between rows of beach rose and across a small peninsula to Edgartown Light, a stubby cast-iron structure offering a clear vista of nearby Chappaquiddick island and Edgartown Harbor.
Back in town, sit down for lunch at Atlantic Fish & ChopHouse. The water views are as delectable as the menu, where the lunch offerings include a lobster reuben, wild salmon, and the “jumbo lump” crab cake. It’s a vacation day, so finish with ice cream at Mad Martha’s.
When you’re ready for the water, you’ve got options. For the full beach experience, take your talents to Edgartown’s South Beach, the island’s most popular sandy destination. Or, if you want something more active, wheel back around to State Beach and rent a kayak from Island Spirit to explore the Vineyard’s north shore and inland harbors. (Tours are also offered.) For a different kind of nature, jump back into your Jeep and head up-island to West Tisbury, the island’s agricultural center and home to Polly Hill Arboretum, a 60-acre preserve named for its late founder; it’s a treasure trove of different plants, trees, and pathways. Polly’s Play Pen, with its sweet mix of English yew, lilac daphne, and many other woodland shrubs and perennials, is a particular favorite.
EVENING: The Vineyard is an island suited to meandering, either on foot or by car. In your Jeep, take Middle Road from West Tisbury into Chilmark. This twisting, turning jaunt cuts past sweeping farmland and a prized pit stop in the form of Chilmark Chocolates. In Chilmark, pick up State Road and continue your southwestern trajectory, slicing between Squibnocket and Menemsha ponds to Aquinnah and its famous beachside cliffs. Watch the endless ocean roll in, until it’s time for a final stop: Menemsha Fish Market, for a lobster roll and a seat by the harbor to watch the sunset.
Finally, make your way back to Oak Bluffs to catch the 8:30 ferry back to Woods Hole. Have some paper and pen ready for the boat ride. You’re going to want to take notes for a longer visit. You’ve only scratched the surface.