There’s something to be said for fall in New England. The crisp air, changing color of the leaves, and bundled up Bostonians sporting their favorite fleece vests mean the season has officially turned. While many travelers flock to Boston in the fall for football, crew tournaments and our legendary fall foliage, we’ve got a secret tip for those wanting to experience something a little more intimate.
Martha’s Vineyard is one of the best-loved summer escapes, but in the fall you can enjoy the best of the island, and all you need is a slightly heavier jacket. Here are a few of our favorite stops around the New England island:
How to get there
First things first: book your boat ride. The Steamship Authority offers daily service from Woods Hole on Cape Cod to Martha’s Vineyard. As the season gets cooler, the boat rides become less frequent. You can reserve a spot for your car on the boat, but make sure you choose your time slots closely — the rides fill up fast, especially in the off-season. The hourlong trip drops you in the town of Vineyard Haven, where you’re free to explore the island.
The Vineyard is divided up into various towns: Edgartown, Oak Bluffs, Vineyard Haven, and Tisbury are the most popular, and also house the most options for staying the night.
The Charlotte Inn, a Forbes Travel Guide Four-Star hotel, is located in the heart of Edgartown just steps from the center of town. If you’re looking for a secret hideaway, this is the place for you. Hidden amongst linden and chestnut trees, The Charlotte Inn is surrounded by landscaped lawns, gardens, shrubs and lines of ivy crawling up the luxe Edwardian-inspired inn.
A little further toward the end of Edgartown is the Harbor View Hotel, one of the largest hotels on the island. The Harbor View Hotel is just steps from the Edgartown Lighthouse — making for ideal picture opportunities — and the center of town. Best recognized by its wrap-around porch and known for its Sunday brunch, the Harbor View Hotel is open year-round to guests.
What to do
Start your day by walking into Edgartown’s town center, where you’ll find various coffee shops and breakfast options. If you’re eager to start your day, make a stop at Espresso Love, a charming coffee shop that serves easy bites such as egg sandwiches and hazelnut chocolate chip scones. Just around the corner from this breakfast spot is where you’ll find retail and boutique shops featuring everything from shoes and scarves to artwork and vintage items. Main and North Water streets contain the highest density of shops, such as Vineyard Vines, The Boneyard Surfshop and Edgartown Books. If you need a pick-me-up while you’re out, stop by Murdick’s Fudge and treat yourself to some homemade fudge (flavors include chocolate peanut butter, Cape Cod cranberry and chocolate walnut, among others) and saltwater taffy.
One thing you’ll love about Martha’s Vineyard in the off-season is less people. Fewer people means less cars on the road, so you can easily journey from town to town in minutes thanks to no traffic and clear roads. Head to the town of Aquinnah, about a 40-minute drive from Edgartown, for a climb to the top of Gay Head Cliffs, and be sure to take some stunning shots of the clay cliffs and lighthouse overlooking Vineyard Sound. In the winter, you can sit among the rocks without anyone around for miles leaving you to simply delight in the crashing waves of the ocean or a long walk on the beach.
End your day in Oak Bluffs (about 40 minutes east of Aquinnah), home to the famous gingerbread cottages and some of the best local joints on the island. Belly up to the bar at Lookout Tavern and savor some of the Vineyard’s craft brews on tap, as well as a bowl of lobster bisque or New England clam chowder, or grab a stool along the back wall of the tavern for unobstructed views of the ocean — a perfect option for watching the sunset on a lazy day.
Photos Courtesy of iStock and The Charlotte Inn