Road Tripping Maine: Our New Favorite Places to Stay, Where to Eat and Fun Things To Do
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Read MoreMARTHA'S VINEYARD: FIRST TIME CRUSH
After a few days in Edgartown, driving “up island” towards Chilmark, I finally understood all the fuss about Martha’s Vineyard. The southwestern half of the island is less populated, more rural with rolling hills, stonewalls, farms and general stores. Turn a corner and you’d swear you’re in the English countryside. And the beaches - the reason that brought me to the Vineyard in the first place - are wilder with dramatic cliffs, rock outcroppings and fewer crowds: absolutely beautiful. Edgartown was a lovely first date, but the villages of West Tisbury, Chilmark and Aquinnah…well they were keepers.
Tripper Tips:
It’s B.Y.O.B. in Chilmark as it’s a dry town… stock up on wine for your stay at MV Wine and Spirits by the airport. The staff is super friendly, knowledgeable and they have a large selection.
When renting a house…visit Beetlebung Farm for fresh produce, eggs and meats. It’s charmingly unmanned, pick what you want, write it down on the yellow pad and leave your money in the tin box.
Everyone claps when the sun goes down in Menemsha. An alternative to dinner is to head down to the beach, bring a bottle of Rose, get some lobsters and watch the sunset on the beach. (Or head to a late dinner after) Don’t think of driving as parking is impossible, instead take the path from the Beach Plum.
Way to go…book a ticket on the frequent ferries from Hyannis, (car reservations must be made well in advance) or avoid the summer traffic to the Cape and head to Quonset Point in Rhode Island to board the boat to Oaks Bluffs, an hour and a half fast ferry.
Stay: The Beach Plum Inn is sweet with just 5 rooms in the main house and 5 cottages scattered over its seven acres. It’s all lush gardens and ocean views of Menemsha Harbor with comfortable, beachy décor and a well-regarded farm to table restaurant that draws crowds for sunset dinners. The biggest bonus: the inn provides parking and walk on passes to both Lucy Vincent and Squibnocket beaches, two of the island's best beaches, private for residents of Chilmark. (Next door, Beach Plum’s sister property, the Menemsha Inn, is larger, more rustic and works well for families with larger cottages.)
On the Way: Driving from the ferry, the airport, or Edgartown, stop for breakfast in West Tisbury at 7a Foods. Order one of their tasty egg sandwiches on a homemade biscuit to eat on the porch with the morning bikers. Get a hippie cookie to enjoy later in the day and their iced coffee, made with a blend of Cocoa Hazelnut from Java Tree. Starting at 11:15 am, 7a starts selling their gourmet sandwiches and salads, perfect for a picnic hamper at the beach. (Vegetarians will be happy ordering the Shitake Umami Tsunami.)
Don’t Miss: Right next door to 7a, Alleys’ General Store has been serving the Vineyard since 1858; browse the aisles for a hit of nostalgia.
Farmers Market: On Wednesdays and Saturdays don’t miss the Farmers Market, held from 9-12, showcasing the goods from more than 40 farmers and purveyors from across the island.
Lunch: After checking into Beach Plum, it’s just a scenic, short walk down a woody path to the beach at Menemsha, a public beach known as the premier spot for sunset on the island. Wander around the working fishing harbor, the colorful fishing boats and shacks present endless photo ops. There is nothing more quintessential New England than eating a lobster on the docks at Larsen’s Fish Market or a basket of fried clams or shrimps at The Bite. Don’t forget to get extra napkins!
Beach: Load up on beach chairs and umbrellas at the inn and spend the rest of the afternoon at Lucy Vincent Beach--it doesn’t get much better. Take a walk down the beach and don’t be surprised when you get to the stretch of beach that’s clothing optional. Walk back along the clay bluffs admiring the rock formations below.
Dinner: State Road is one of those restaurants that you want to order everything on the menu—and you can’t go wrong—it is a delicious meal, from start to finish, right down to the excellent wines served by the glass.
Day Two:
Provisions: Have breakfast at Beach Plum or head to the Chilmark General Store and eat on the porch. Get some sandwiches and snacks to take to the beach. Buy a few of the 1 lb. bags of Chilmark Coffee Company, made on the island, to bring home.
To the Lighthouse: It’s a beautiful drive to Aquinnah, formerly called Gay Head, to visit the historic lighthouse and the Gay Head Cliffs on the westernmost point of the island. The light was dark for the last few months, as the lighthouse was carefully moved back 120 feet due to eroding cliffs. Climb the small hill past the shops of the Wampanoag Indians for incredible views of the cliffs and ocean below.
Back to the Beach: Another day, another unique beach—that’s what makes Martha’s Vineyard special. Go early to get a spot at the small parking lot of Moshup Beach. It’s a nice 10-minute walk down to the beach. This was my favorite beach; the multi colored cliffs a stunning backdrop, changing colors with the light. It’s also beautiful in the late afternoon. If you want to visit another beach venture to Squibnocket where the surfers hang out.
Dinner: It’s Chef Chris Fischers’ second season at the helm of the restaurant at the Beach Plum, with much of the produce coming from his nearby family’s Beetlebung Farm. At dusk the lawn starts filling with couples sipping wine, children playing ball or chasing the roaming chickens and wild turkeys; all getting ready to watch the day fade away and dine on the seasonal farm to table menu. Or head to Chilmark Tavern, Jenna’s Sprafkin’s casual American bistro, featuring a seasonal, creative menu using mostly local products. Highly recommended!
Don’t Miss: Before returning home, have breakfast at the Art Cliff Diner. Go early to avoid a long wait, it’s popular for a reason—you’ll understand after your meal of spicy chicken hash and eggs, breakfast tacos or delicious fresh made scones or waffles.
Related Destinations
MARTHA'S VINEYARD: SUMMER DAYS IN EDGARTOWN
Get to the ferry early to claim a seat on the upper deck, rummage in your bag for your book and sunglasses, and then let out a deep breath. Your vacation officially starts as soon as the boat pulls away from port. Martha’s Vineyard, an island just off the coast of Cape Cod in Massachusetts is known for its magnificent beaches, picturesque harbors and historic, charming villages. Made up of six distinct towns, the Vineyard is much larger than its sophisticated, nearby rival island of Nantucket. Based in colonial Edgartown, DT365 shares our highlights for a few relaxing days at the beach.
Tripper Tips:
Renting a house…pick up provisions at Morning Glory Farm. In addition to delicious baked goods and beautiful produce they have an impressive array of cut flowers.
Another world…Take the Chappy Ferry from Edgartown to Chappaquiddick Island. Visit Japanese Mytoi Garden, Wasque Point, Leland Beach, Norton Beach, or Cape Pogue Wildlife Refuge.
Craving some fried clams or a lobster roll…Skip the touristy Seafood Shanty and get fried clams to go at their take away stand, The Quarterdeck.
Way to go…book a ticket on the frequent ferries from Hyannis, (car reservations must be made well in advance) or avoid the summer traffic to the Cape and head to Quonset Point in Rhode Island to board the boat to Oaks Bluffs, an hour and a half fast ferry.
Stay: A short walk into town, check in to the Harbor View Hotel: a waterfront property overlooking the beach, Edgartown Lighthouse, and Chappaquiddick Island. Splurge on one of the cottages or stay in the main building. For those who prefer to be close to the beach, the Winnetu Oceanside Resort in nearby Katama is just a path away from South Beach, a beautiful stretch of sandy beach. Winnetu is great for families, with a kids program and tons of room options to accommodate all. For a quieter, more formal stay, check in to The Charlotte Inn, less beachy and reminiscent of an English country house.
Ride: Harbor View can arrange to have a bike delivered directly to the hotel, or rent a bike in town at Martha’s Bike Rentals or Edgartown Bicycles and Rentals. Make sure to request a basket to hold your towel and refreshments for the beach.
Morning Grub: Grab a coffee and some freshly made baked goods at Espresso Love. Or head to tiny diner Dock Street Coffee Shop, an island institution, for one of their breakfast sandwiches. I liked the shady terrace at Behind the Bookstore Café, located directly behind Edgartown Books with a eclectic, healthy menu and excellent coffees and teas.
Lunch at the Beach: Get a gourmet sandwich or salad to go before leaving Behind the Bookstore and ride your bike to South Beach for the day. Once out of town, follow the 4-mile flat bike path direct to the beach. If you have a car, or choose to take a taxi, Harbor View has beach chairs you can use. (Taxis are plentiful on the island.)
Wander: Spend the late afternoon walking around downtown Edgartown, in and out of the upscale shops, indulging in some fudge at Murdick’s or an ice cream at Mad Martha’s or Vineyard Scoops. Across from the Harbor View, walk out to the Lighthouse and then down the rocky, narrow beach, returning back by the streets and admiring the beautiful oceanfront homes and rows and rows of hydrangeas.
Dinner: I don’t usually order fried foods, but the wok fried whole lobster has quite a reputation at Atria, set in a classic New England house just on the edge of town. The restaurant is divided in two: upstairs is quieter; finer dining while downstairs is a casual cellar bar. Both offer the same menu, with the cellar only offering an extensive burger selection, considered some of the best on the island. And the star of the show—the lobster served whole atop buttery mashed potatoes and island greens—may just be one of the best lobsters I’ve ever had.
Day Two
Get Moving: Get back on your bike, proceeding cautiously out of town, till you get to the bike path heading towards Oak Bluffs. This is a longer ride, clocking in around 8 flat, easy miles. At the dividing line between the two towns, stop to watch the jumpers at “Jaws Bridge”, (The American Legion Memorial Bridge) made famous in the 1975 blockbuster film. Crowds gather to leap and cheer each other on--in direct defiance of the sign that says no jumping. Kayaking and paddle boarding can be organized right across the road on Sengekontacket Pond. Continue on, arriving at Methodist Campground, a cluster of charming multicolored gingerbread cottages surrounding an open-air Tabernacle dating back to 1879. It is surreal to see the different architecture; in direct contrast to the stately whaling mansions in Edgartown.
Lunch: I know I’m going to crave the Fried Green Tomato BLT for a long time from Slice of Life on Circuit Avenue, in the heart of Oak Bluffs’ main shopping street. Go ahead and order the truffle fries, you’ll burn it off on the bike ride back to Edgartown. Other popular spots in Oak bluffs include Nancy’s for seafood, Giordano’s for fried clams and pizza (take out only), and the Red Cat Kitchen for dinner.
Sweet Tooth: Martha’s Vineyard Gourmet Café & Bakery serves their beloved donuts and apple fritters all day long at their bakery storefront, but the real action takes place starting at 7:30PM –till 1AM where people wait on line at the back door for hot, right out of the oven doughnuts. It’s become so popular that everyone refers to the bakery as Back Door Donuts. Ben & Bill’s Chocolate Emporium has the best ice cream on the Vineyard served in their old fashioned charming store.
Stroll: Oaks Bluffs has a whole different feel than Edgartown, it’s touristy for sure, yet lively, it just feels like a summertime beachside town that could be down the Jersey Shore or at Delaware’s Dewey Beach complete with arcades, harbor side clam bars and old movie theaters. You must stop and watch the kids exuberantly grabbing for gold rings at the Flying Horses, the nations oldest platform carousel, designated a national landmark. Oak Bluffs has its own unique vibe and personality, the fun “cousin” to Edgartown’s elegant “aunt” and it’s worth visiting.
Dinner: The Port Hunter doesn’t take reservations, but it’s well worth the wait. Have one of their specialty cocktails and an appetizer at the bar or communal tables and soon you’ll be trading stories with your neighbors. The creative seasonal menu is locally sourced, and there’s a raw bar for oyster fans. On Tuesdays, Thursdays, Fridays and Sundays starting at 10 pm, half the tables are cleared away to make way for live music sets. Don’t miss dining here!
Related Destinations
MAINE: ACTIVE DAY ON MOUNT DESERT ISLAND
Mount Desert Island, Maine (MDI) is a small gem of an island combining lakes, mountains, ocean, and the East Coast’s oldest national park, Acadia, into a single destination. Our good friend, Jon, travels to MDI every summer and knows all the best spots. Jon recommends you allot several days to fully explore the island, but offers these suggestions for what a perfect day might look like.
Tripper Tips:
Book well in advance… Acadia attracts tons of visitors in the summer months. Many families choose to stay at the Bar Harbor Inn or at the Harborside Hotel, Spa and Marina. For a quieter stay, try the Ullikana, a B&B overlooking Frenchman Bay or The Asticou Inn, located in Northeast Harbor.
When to Go…The peak summer season runs late June through Labor Day. Fall brings spectacular foliage and winter’s the time for excellent cross-country skiing.
Early Morning: You’ll thank yourself later for getting up at dawn to catch the sunrise on Cadillac Mountain, the highest peak on the East Coast at 1,532 feet. Enter the park near Bar Harbor, drive up the winding road, and join the blanket-wrapped masses to see the sunrise before anyone else in the United States. It’s a sight you’ll long remember. Make sure to check the exact time before you go, and give yourself an extra 20 minutes for the drive up the mountain.
Morning Meal: Once the sun is up, head into Bar Harbor for breakfast. Jordan’s Restaurant opens at 5am, and will welcome you (and local lobsterman) with friendly service and quality diner fare. If you can wait until 7am to eat, other more upscale options are Café This Way and Two Cats. Blueberry pancakes are a tradition for breakfast in MDI, but lobster eggs Benedict is quickly becoming another favorite. Eat well — you’re going to need the fuel.
Hit the Trails: One of Acadia National Park’s most beloved features is the 40+ miles of carriage roads. John D. Rockefeller spent thirty years supervising and financing the creation of a network of broken-stone roads free of motorized vehicles that make the park one of the most beautiful and bike-friendly destinations in the US. You can rent bikes at the Bar Harbor Bicycle Shop, then either drive or hop on the free Island Shuttle busses to Eagle Lake parking lot. You could bike around Eagle Lake (a 6 mile loop), or if you’re feeling adventurous, continue further to Jordan Pond House, which is famous for popovers and jam.
Scenic Road: Another option is to get back in your car after biking, re-enter the park near Bar Harbor, and drive the Park Loop Road — 27 miles of postcard-worthy Maine scenery. A park pass is needed, but the funds are an important part of maintaining Acadia’s beauty. You’ll want to pull over often to take pictures and explore some of the footpaths along the coast. Keep an eye out for Sand Beach (a rarity along a rocky Maine coastline), and Thunder Hole, where waves collide loudly with land.
Lunch: Next, head to the western half of the island, known as the “quiet side.” If you’re hungry, pull over at Mother’s Kitchen in Town Hill. It’s a small stand-alone building next to a hardware store, and serves popular gourmet sandwiches made with local, organic ingredients. Another option is to drive into Southwest Harbor and stop at either Eat-a-Pita (which has much more than pita, and offers outdoor seating) or Little Notch Café, which features artisanal breads, pastries, and pizza, all made expertly in their own bakery. (There is also a Little Notch Bakery outpost in Bar Harbor.)
Get moving: Next, it’s time to work off lunch with a hike and a swim. There are many great hikes in Acadia, from easy strolls along the shore to iron-rung trails like the Precipice and Beehive trails. (Not for the faint of heart) A good guidebook with maps and descriptions is essential. On your way out of Southwest Harbor, you could explore a good moderate trail by parking at the Echo Lake parking lot and hiking up the Acadia Mountain or St. Sauveur trails. These are loops that have the advantage of ending at Echo Lake so you can swim afterwards.
Stay Moving: Another option on the quiet side is to drive to the end of Beech Hill Road and hike the Beech Mountain Trail up to the fire tower, which is a good workout and offers summit views of the surrounding islands, or the Canada Cliffs trail, which has spectacular views of the Cranberry Islands and Echo Lake. Stay on the lookout for blueberries as you hike — in late July and early August, they are all along the trails.
Farm Market: Once you’re back in the car, you’ll pass Beech Hill Farm, a sustainable 73-acre farm run by the College of the Atlantic and offering great local vegetables, flowers, dairy, other organic goodies. You could then take a quick swim at nearby Long Pond (which also rents kayaks and canoes), or the smaller Somes Pond favored by locals.
Dinner: After a well-deserved nap, it’s time for dinner, and nothing says mid-coastal Maine like fresh lobster. There are many options for great lobster on the island. Two favorites are Beal’s in Southwest Harbor, which has a fun, family-friendly vibe overlooking the harbor, and Thurston’s in Bass Harbor, which added a full bar two years ago. Thurston’s serves IslandBound Treats’ excellent berry pies for dessert. You can’t go wrong with either, but be patient because the lines can be long and cooking lobster takes time.
After-Dinner Fun: Assuming you left room for ice cream (come on, you’re on vacation), swing by Mount Desert Island Ice Cream back in Bar Harbor. Their Maine Sea Salt Caramel ice cream is amazing, but they make many unusual gourmet flavors and gladly let you try samples. Then while exploring the town’s many shops, you could check out the newly restored Criterion Theater, built in 1932, which features movies, music, and more in a 1932 Art Deco setting, or play Bocce at the Lompoc Café and grab a local craft beer while you share highlights of your day on MDI.
