20 best weekend getaways from Boston

Nantucket is the place to be once the sun is shining. 

Eat at: or, The Whale (38 Main St, 508-825-5897) located right on the cobblestoned main street in downtown Nantucket, if the weather is still nice you can enjoy eating on or The Whale’s back patio.

Stay at: Hotel Pippa (5 Chestnut St, 508-228-5300) at the contemporary boutique hotel, guests can enjoy complimentary breakfast before setting out for the day. The team at Hotel Pippa is happy to assist guest booking a variety of island activities from fishing expeditions to cooking classes. When the day is done, guests can unwind on Hotel Pippa’s cozy patio. 

Must do: Visit in early October and travelers can enjoy a brand-new fall festival, The Harvest Fair (220 Milestone Rd) which will take place October 1-2. Historically the Island Fair and the Cranberry Festival happened on separate weekends but 2022 will be the first year the events merge for one large festival.

Step back in time with a weekend getaway to Newport, RI. Home to the famed Newport Mansions, Newport is also packed full of waterfront dining, shopping, and plenty of options for getting outside and staying active.

Eat at: The Mooring Seafood Kitchen & Bar (1 Sayers Wharf 401-846-2260) pro-tip is to reserve a table around sunset on their deck overlooking the wharf. 

Stay at: For a romantic getaway in Newport check in at Castle Hill Inn (590 Ocean Ave 888-466-1355), the views cannot be beat. 

Must do: Touring the Newport Mansions is a must, we recommend doing at least three. But save The Breakers for last as it is the most impressive! Afterwards, stroll along the Cliff Walk for world class views. Last, no trip to Newport is complete without a sail around the harbor, book an afternoon sail or an evening cocktail sail on the Adirondack II.

One of the most charming towns in all of New England. Woodstock is the perfect fall escape, travelers can visit local farms, museums, stroll through the town square and pop in and out of all the local shops.

Eat at: Worthy Kitchen (442 Woodstock Rd, 802-457-7281) definitely worthy of a visit. At Worthy Kitchen guests will find farm-to-table comfort food and local craft beers on tap.

Stay at: The Woodstock Inn & Resort (14 The Green, 888-338-2745) located right on the town square The Woodstock Inn is the perfect place to stay if you want to be centrally located to everything in town. Walking distance to tons of shops and restaurants, the Inn also has a world-class, LEED-certified Spa.

Must do: Sugarbush Farm (591 Sugarbush Farm Rd, 802-457-1757) offers free cheese and maple syrup tastings. You can explore the farm grounds, take in beautiful foliage views and do a little shopping in their farm store. If you’re visiting Woodstock in the fall, you have to take a ride out to Sleepy Hollow Farm (3429 Cloudland Rd South, Woodstock, VT 05091). A privately owned property, but you can view the charming farm from the road, you’ll likely be in good company with fellow photographers and leaf peepers.

Leave the car at home because Provincetown is just a 90-minute ferry ride from Boston. With lots of fun bars, great restaurants, and plenty to do Ptown is one of our top weekend getaways from Boston for a reason.

Eat at: The Canteen (225 Commercial Street 508 487-3800) has beach front dining, an incredible lobster roll, and frosé. What more could you need?

Stay at: The Harbor Hotel Provincetown’s (698 Commercial St, 508-487-1711) retro-glam style and modern amenities makes it exactly what you want on a weekend away. Plus they’re pet friendly!

Must do: Enjoy off roading on a dune tour. Stop by Art’s Dune Tours for an exhilarating ride through the dunes, the team gives you a full history of the area, from how it joined the Cape Cod National Seashore to the history behind the artist shacks.

Taylor Swift vacations in Watch Hill, why shouldn’t you? Just over two hours from Boston this small town is walkable and is home to the oldest continuously operating merry-go-round in the country.

Eat at: Olympia Tea Room (74 Bay Street 401-348-8211) is an institution. Just a short walk from the beach the simple menu has been keeping guests happy for over 100 years. 

Stay at: There are two clear winners when it comes to where to stay, the Ocean House (1 Bluff Avenue 855-678-0364) or the Watch Hill Inn (38-44 Bay Street 855-677-7686). The Ocean House boasts its own private beach, multiple onsite dining options including Dalia, a new seasonal Coastal Mexican venue by Chef Dantón Valle, and croquet courts. The Watch Hill Inn is right on Bay St overlooking the harbor, and is convenient to all the shops.

Must do: Walk down to the Watch Hill Lighthouse, then spend the day shopping along Bay Street or head to the beach.

Just an hour and a half from Boston, Kennebunkport is the quaint seaside town you’ve been dreaming of. There is a little something for everyone in Kennebunkport (you may even spot the Bush family!). 

Eat at: Stop by Old Vines Wine Bar (173 Port Road (207) 967-2310) for outdoor seating and live music, their menu is filled with small snacks and sharables plates. However, the wine list and craft cocktails are the real draw. And no trip to Kennebunkport is complete without a stop at The Clam Shack (2 Western Ave 207.967.3321), they’ve been serving fresh seafood since 1968!

Stay at: The Boathouse (21 Ocean Ave; 207-967-8225) brushes up against the Kennebunk River, which is easily viewed from your room’s oversized windows.

Must do: Visit Nubble Light. If you went to Kennebunkport for the weekend and didn’t take a picture of the famous lighthouse, did you really go?

Home to Mystic Pizza and the Mystic Aquarium, this small coastal village, which is actually officially part of Stonington CT, is a great weekend getaway from Boston. 

Eat at: Mystic Pizza (56 West Main St. 860-536-3700) is worth a visit. But if you’re not in the pizza mood checkout Red 36 Bar & Grill (2 Washington Street 860-536-3604) for waterfront dining, fresh seafood and great cocktails.

Stay at: Stonecroft Country Inn Bed and Breakfast (515 Pumpkin Hill Road 860-744-5868) is the quaint B&B that summer weekend getaway dreams sometimes require.  

Must do: Go brewery hopping. Mystic and Stonington are home to a handful of great local breweries including Barley Head Brewery, Bank & Bridge Brewing and Beer’d Brewing Co. Not into beer? There are also a bunch of great vineyards and wineries in the area.

In need of fresh air? The Berkshires have you covered with museums, concerts, legendary authors’ homes, hiking and more. 

Eat at: Methuselah Bar and Lounge (391 North St, Pittsfield; 413-347-2888) is focused on organic wines and craft beers, pairing them with funky, reimagined American fare, tacos and Korean-inspired dishes. Nudel: Comfort & Craft (37 Church St. 413-551-7183) post-pandemic this Berkshires favorite has been doing “pop-ups” that allows them to change their menu every few months to focus on fresh seasonal ingredients! 

Stay at: Seven Hills Inn (40 Plunkett St 413-637-0060) the former Gilded Age mansion offers 57 guest rooms, stunning gardens and an outdoor pool.

Must do: Be adventurous at Catamount Mountain Resort (Route 23 413-528-1262) go on a zipline tour, spend the day in the adventure park, or go on a scenic chairlift ride!

A little further afield, Bar Harbor is almost five hours from Boston by car so be sure to make the most of your weekend in Bar Harbor and add on a trip to Acadia National Park, the only national park in New England

Eat at: The Travelin Lobster (1569 ME-102 207-288-8028), have the lobster roll you won’t regret it.

Stay at: The Bar Harbor Grand Hotel (269 Main Street 207-288-5226) is a replica of the historic Rodick House, convenient to both downtown and Acadia. This hotel is the perfect spot to relax and unwind after a day of hiking.

Must do: Make the most of your weekend in Bar Harbor by doing a tour of Acadia National Park. Thsi is the most approachable way to see the park if you’re not a big hiker and want to see all the major landmarks in a short period of time. (The classic tour is only 2.5 hours leaving you plenty of time to explore on your own!)

Even if you don’t know it, when you think of New England you are likely picturing the Kancamagus Highway. The scenic highway runs right through the heart of the White Mountain National Forest. The White Mountains are truly spectacular in the fall and winter, there are tons of charming small towns to stay in, great hiking and of course endless vistas.

Eat at: The Covered Bridge Farm Table Restaurant (57 Blair Rd, 603-238-9115) something about wood covered bridges just captures the essence of New England perfectly. The Covered Bridge Farm Table Restaurant is located at the bottom of the White Mountains and is the perfect spot to stop for lunch on your drive up or your drive back to Boston.

Stay at: The Omni Mountain Washington Resort (310 Mount Washington Hotel Rd, 603-278-1000) this historic New England hotel has views of the presidential mountain range, a world class spa and you can take a scenic gondola ride right across the street at Bretton Woods.

Must do: The Cog Railway (3168 Base Station Rd, 800-922-8825) want to take in the foliage from the summit of Mount Washington but not looking to take on the hike? The Cog Railway will take you on a dramatic climb up the mountain. The rail has been running for more the 150 years, be sure to book tickets ahead of time so you can take in the views on this must do experience.

Martha’s Vineyard is just a short ferry ride from Cape Cod that drops travelers right in either Edgartown, Oak Bluffs or Vineyard Haven for convenient access to shops, hotels and restaurants. Enjoy amazing beaches, see the Edgartown Lighthouse or take a ride to Island Alpacas for a truly one-of-a-kind experience.

Eat at: Visit Back Door Donuts (1-11 Kennebec Ave 508-693-3688) for the ultimate late-night snack, these donuts are worth waiting in line.  

Stay at: The Harbor View Hotel (131 N Water St 877-624-7992) cannot be beat. So many things including amazing views, sumptuous accommodations, complimentary bikes and the Mercedes-Benz Drive Program make it a luxurious home away from home. 

Must do: Whether using complimentary bikes provided by a hotel or renting bikes for the weekend, bikes are one of the best ways to explore the island. Martha’s Vineyard offers over 40 miles of trails and roadways through its scenic towns and along its coast.

Located just 13 miles offshore, Block Island is a great alternative to Nantucket or Martha’s Vineyard, it is a bit quieter and more relaxed. Good news for our nature lovers, 40% of the island is conservation land, accessible only by bike or foot.

Eat at: Poor People’s Pub (33 Ocean Ave 401-466-8533) offers casual local seafood, burgers, pizza and more. They’re conveniently located by the Old Harbor Block Island Ferry and offer outdoor seating! Before heading back to the ferry, grab gourmet sandwiches from Three Sisters (443 Old Town Rd; 401-466-9661).

Stay at: Spring House (1401 Ocean Ave; 732-776-6700), the island’s oldest hotel, entices with Adirondacks and a wraparound veranda overlooking the water. 

Must do: Go horseback riding on the beach. Visit Rustic Rides Horse Farm, the offer both beach rides and trail rides, a great way to see the island!

Want to get witchy? Salem attracts thousands of visitors every fall, people looking to embrace the spooky, supernatural, and witchy vibe of the small coastal town. It can get a little crazy in the two weeks leading up to Halloween, but a winter trip is just as fun! In addition to all the witch themed attractions there is also a buzzing art scene in Salem, great restaurants and travelers have to visit Far From the Tree Cider to do a tasting.

Eat at: Howling Wolf Taqueria (76 Lafayette St, 978-744-9653) keep things spooky with a red-hot ghost pepper infused margarita. Howling Wolf Taqueria is known for their massive burritos and their wolf bites like avocado fries and ceviche.

Stay at: The Merchant (148 Washington St, 978-745-8100) a Lark Hotel, The Merchant is conveniently located right down town. Walk to all the witch shops, great restaurants and plenty of nearby tours and museums.

Must do: If you want to embrace the spooky vibes in Salem sign up for a Candlelit Ghostly Walking Tour (288 Derby St, 978-740-2929). The hour long walking tour will take you around some of Salem’s most haunted locations. For travelers who want to see another side of Salem, plan a visit to the Peabody Essex Museum (161 Essex St, 978-745-9500) the world-renowned art museum has collections dating back to the 1700s including paintings, sculptures, photography and more.

Charming brownstones, bucket list worthy restaurants and ocean views? Portland is a great idea any time of year but especially in the summertime when you can take advantage of everything happening on the waterfront. Be prepared to eat all weekend long, Portland is a foodie’s paradise.

Eat at: You really can’t go wrong but three spots to get you started: Duckfat (43 Middle St; 207-774-8080) for fries, poutine and a milkshake when you’re hungover the next day. Central Provisions (404 Fore St; 207-805-1085) for the locavore meal of the moment. And you must try Highroller Lobster Co (104 Exchange St. 207-536-1623)!

Stay at: Conveniently located in the Old Port, The Press Hotel (119 Exchange St; 800-971-2000) is the former home of the Portland Press-Herald and carries on the print tradition with newspapered walls, letterpress carpeting and leather desk chairs. Be sure to check out their amazing art collection.

Must do: Tour Casco Bay! Experience Portland on the water as you visit all the islands throughout Casco Bay.

Hartford is the perfect central location for several fantastic fall attractions tucked away in the heart of Connecticut. Stay in Hartford and plan a drive to East Hampton, home to Pumpkintown USA. Then book a fall foliage scene hot air balloon ride with CT Ballooning in Kensington.

Eat at: Max Downtown (185 Asylum St, 860-522-2530) a staple in Hartford for over 20 years this chophouse and whiskey bar is a must visit during your stay in Hartford. Dine in style and enjoy elevated classic in the recently renovated space.

Stay at: Delmar (1 Memorial Rd, 860-937-2500) this pet-friendly, luxury hotel is the perfect place to enjoy a weekend getaway to Hartford. The Delmar has a full-service spa, the fitness center features Peloton bikes and guests even get complimentary admission to the New Britain Museum of American Art. 

Must do: Use Hartford as your jumping off point to explore some of Connecticut’s best fall attractions like Pumpkintown USA (100 East High St, East Hampton CT). If you want to spend a day exploring Hartford, plan a visit to Mark Twain’s House and Museum (351 Farmington Ave, 860-247-0998).

New England is awash with winter resort towns, but we most love those areas that celebrate four-season recreation. Come summer, Stowe swaps out skiing for hiking, golfing, mountain biking and kayaking. Bonuses include swimming hole visits and scenic drives up the squiggly Auto Toll Road.

Eat at: Plate (91 Main St; 802-253-2691) combines California cuisine with Vermont-sourced ingredients. Take the gondola up to Cliff House (5781 Mountain Rd; 802-253-3665) and enjoy a bottle of wine on the outside deck before hiking down afterward.

Stay at: Spruce Peak (7412 Mountain Rd; 802-253-3560) manages to feel homey and warm (also dog-friendly!), despite its luxury amenities. Added perk: It’s also dog friendly, so your canine companions can come stay on vacay.

Just a short ride from Boston, this seaside town has a rich history. While you may think it was the town’s role in the American Revolution or its history as a booming seaport that put it on the map, but Portsmouth is actually most well known as a hub for the brewing industry. There are 8 breweries travelers can visit right in Portsmouth!

Eat at: Botanica Restaurant and Gin Bar (110 Brewery Ln, 603-373-0979) this upscale French-influenced restaurant is the perfect spot for a romantic dinner, be sure to save room for dessert!

Stay at: Ale House Inn (121 Bow St, 603-431-7760) this boutique hotel is located right in the heart of downtown in what was once a warehouse for The Portsmouth Brewing Company.

Must do: Schedule your visit in October so you can partake in the annual Pumpkin Smash, taking place on Saturday October 28. All month-long travelers can check out the Scarecrows of the Port, unique scarecrow displays scattered throughout downtown.

One of the more underrated New England capitols, Providence also has an incredibly underrated food scene! This city is just a short ride on the commuter rail from Boston and is filled with New England charm and unique events like WaterFire.

Eat at: Hemenway’s (121 South Main St, 410-351-8570) is a top rated and local favorite. Hemenway’s offers an excellent raw bar and is the go-to restaurant for fresh seafood. If you’re looking for a great glass of wine, you’re in luck, in 2021 Hemenway’s received the Wine Spectator’s Award of Excellence.

Stay at: Graduate Providence (), formerly the Providence Biltmore this historic hotel recently got a complete renovation while maintaining some of the historic charm, like the lobby’s original ornate ceiling and glass-and-brass elevator. Located right downtown, guests are just a short walk to restaurants and shops.

Must do: Head to the Roger Williams Park Zoo (1000 Elmwood Ave, 401-785-3510) for the annual Jack-o-lantern Spectacular. Starting September 29 and running through October 31 visitors can take in thousands of artistically carved pumpkins. Throughout fall there will be 4 full lightings of WaterFire, a series of up to 100 bonfires floating on the three rivers of downtown Providence. See this award-winning installation on September 24, October 1, October 22, or November 5.

The Cape is a no-brainer, but where to stake your claim? We’ve long migrated towards the inimitable charms of Chatham, where the homes will make you drool, the town center is walkable and crammed with cute boutiques, and the seafood is hauled in just offshore. 

Eat at: Impudent Oyster (15 Chatham Bars Ave, 508-945-3545) offers innovative spins on classic seafood dishes and a lively bar inside a former church.

Stay at: Chatham Bars Inn (297 Shore Rd; 508-776-6700) is the ne plus ultra of Cape retreats for good reason: The cabana’d beach alone earns the resort its mythic reputation—and justifies the indulgence.

If you must flee the country, you might as well drive into the clutches of a cosmopolitan city bursting with history, nightlife, outdoor concerts and a shopping scene that invites closet do-overs.

Eat at: Martin Picard’s Au Pied de Cochon (536 Duluth Est; 514-281-1114) for foie gras on top of foie gras on top of poutine.

Stay at: Hotel Gault (449 St. Helene St; 514-904-1616), a lavishly reappointed boutique hotel in Old Montreal.