5 charming New England towns you can drive to from Boston

June 04, 2020

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13 min read

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While a typical summer weekend in Boston usually means a stroll along the Charles River or a picnic in the Common, we all know this summer won't be anything close to normal.

Travelers who need a change of scenery can find charming New England towns and untouched stretches of wilderness just a few hours from the city.

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From Boston, travelers can reach many exciting and overlooked destinations, such as the vertical granite cliffs of Camden Hills State Park and historic towns filled with lovely Victorian homes. If you're planning on spending more time in the great outdoors than ever before, there are plenty of opportunities for adventure-fueled days spent rock-climbing, hiking and kayaking.

Whether you're planning a road trip from Boston this summer or a year from now, remember that small New England towns are filled with intimate B&Bs and historic inns, be sure to book with a credit card that will help you maximize your travel purchases, such as the Chase Sapphire Reserve® (3x) or Chase Sapphire Preferred® Card (5x when booked through Chase Ultimate Rewars,2x on all other).

And be sure to keep a great card for earning points on gas purchases in your wallet, too — especially if you're driving three hours or more outside Boston. With the Citi Premier® Card, you'll earn 3x points per dollar when you fill up at gas stations, along with 3x points on air travel, hotels, restaurants, and supermarkets and 1 point per dollar on everything else — ideal for a long weekend exploring New England, staying in charming inns and eating as much clam chowder as you can stomach.

If you're planning a near-term road trip, just remember that many states may still require out-of-state travelers to self-quarantine for two weeks. Maine's executive order, for example, requires a 14-day self-quarantine for visitors through much of the summer. Plus, many inns, restaurants and attractions may remain closed, at least to out-of-towners. So, you might want to bookmark these itineraries for later.

Camden, Maine

Distance from Boston: 3 hours and 20 minutes

Often overshadowed by nearby Bar Harbor, Camden is a haven for outdoorsy travelers. Sure, visitors can spend an afternoon wandering up and down Main Street, stopping to admire the views of Camden Harbor or peruse the boutique shops (be prepared to spend too much on unexpected finds at Josephine on Elm Street). But to make the drive — just over three hours — worthwhile, travelers should take advantage of the destination’s ample outdoor activities.

What to do: Explore Camden Hills State Park on the 30-mile trail network. One of our favorites is the moderate trail up to Ocean Lookout for an uninterrupted view of the town and harbor. If you’re interested in something more, well, vertical, have Equinox Guiding Service bring you out for an afternoon of rock climbing. For a more relaxed option, head out to Savage Oakes Vineyard and Winery to sample their house blends, made with 10 grape varieties grown on-site.

Where to stay: Camden has a mix of lodging options, mostly small bed and breakfasts and inns. But 16 Bay View is Camden’s newest luxury hotel, housed in a 100-year-old industrial brick building that once operated as a car dealership. For a more intimate stay, book a room at the Camden Harbour Inn, with rooms and suites that boast (as its name implies) exceptional views of the water.

What to eat and drink: Located in the Camden Harbour Inn, travelers should reserve a table on the porch of Natalie’s Restaurant. If oysters are what you’re after, head over to 18 Central Oyster Bar and Grill, in nearby Rockport, for a platter of their local or “away” raw oysters.

Freeport, Maine

Brewster House Bed & Breakfast. (Photo courtesy of Brewster House Bed & Breakfast/Facebook)

Distance from Boston: 2 hours

While Freeport is best known as the birthplace of LL Bean, there are plenty of other reasons to spend a weekend in town. Located just north of Portland on the shores of Casco Bay, brick buildings line Freeport’s streets, and shoppers wander unhurried between the outlet stores and seafood-centric restaurants.

What to do: Start your trip to Freeport by stocking up on activewear and outdoor gear at LL Bean's flagship location, which is typically open 24 hours every day. Shoppers should also check the outlets at the Freeport Village Station. Just be sure to keep a great card for everyday spending, such as The Blue Business® Plus Credit Card from American Express or the Chase Freedom Unlimited, in the front of your wallet. Afterward, head over to DeLorme, in nearby Yarmouth, to see the world’s largest rotating globe (it’s nearly 42 feet across), or take a walk through the hemlock and white pine forests of Wolfe’s Neck Woods State Park.

Where to stay: The Brewster House Bed and Breakfast is an upscale inn just three blocks from the center of Freeport. Seven rooms and suites make this a great choice for a romantic getaway, or for families exploring coastal Maine. Another option is the Harbour Towne Inn on the Waterfront — a Victorian-style bed and breakfast with panoramic views of Boothbay Harbor.

What to eat and drink: Start the morning with a cup of the daily roast from Coffee By Design, a sustainable cafe located inside the LL Bean store. Linda Beans is a favorite for seafood (order the classic Maine lobster roll) right on the main strip. Outdoor seating with fire pits makes this a great spot during cool, early summer evenings. Visitors should also sample Maine Distilling’s Blueshine blueberry liquor when the distillery is open for tastings.

Stockbridge, Massachusetts

Distance from Boston: 2 hours

Surrounded by the mountainous terrain of the Berkshires, Stockbridge is a small town in rural Massachusetts with the culture and arts scene of a big city — with none of the traffic or crowds. Summers are usually filled with music festivals and theater, and travelers can also explore the area’s extensive hiking and biking trails.

What to do: Founded in 1934, the Berkshire Botanical Garden (closed until further notice) is a 15-acre public garden that showcases local flora alongside contemporary sculpture exhibitions. Need a more strenuous activity? The Laurel Hill Association maintains three hiking trails in the Stockbridge area — the Mary Flynn Trail, Laura’s Tower Trail and Ice Glen Trail. After a day of hiking or strolling through the gardens, travelers can typically catch an opera or theatrical performance at the historic Mahaiwe Performing Arts Center (closed until further notice). And, if you have the time to dedicate during your weekend trip, head to the Kripalu Center for Yoga and Health (closed for the remainder of 2020), a retreat offering a mix of yoga, writing and Ayurveda courses, among others. Programs typically last for at least two days.

Where to stay: The Stockbridge Country Inn is located within walking distance of multiple area museums. Its location on four acres of manicured lawns and gardens, complete with a patio and heated outdoor pool, make it a great place to relax and enjoy a hot summer afternoon. The Inn at Stockbridge is another option, with 15 rooms spread throughout a renovated barn, a Victorian-style mansion in which many original antiques remain and a cottage house. When Miraval finally welcomes visitors to its third resort in the Berkshires, guests can focus on wellness and mindfulness. After all, it wouldn’t be a Miraval resort without a full spa experience. Miraval resorts occupy their own lane in the World of Hyatt award chart, and a free night will cost you 45,000 points, plus an additional 20,000 per night for an additional guest in your room.

What to eat and drink: Providing food and accommodations to visitors for over two centuries, The Red Lion Inn serves traditional New England cuisine (along with an expansive wine list featuring over 400 different selections). For classic European dishes (think: escargot pot pie), try Once Upon a Table, which also dishes up more hearty, regional fare (crab cakes, for example).

Woodstock, Vermont

Distance from Boston: 2.5 hours

Located in the heart of the Green Mountains, Woodstock is the quintessential New England town. New openings and upgrades over the past few years have transformed this drive-by town into a popular (and rather upscale) getaway for New Englanders. A pedestrian-friendly downtown is filled with small shops, inns and restaurants, while the surrounding rural landscape invites visitors to explore and unwind.

What to do: As the Northeast’s premier skiing destination during the winter months, many of Vermont’s ski resorts are overlooked as soon as the snow melts. For this reason, the local ski hill, Suicide Six, has a new mountain bike park, which has miles of machine-built trails that are free to use. If extreme sports are not for you, take a tour of the Billings Farm & Museum when it reopens (you’ll get a firsthand look at what farm-to-table actually means). Woodstock and the surrounding hills are also great for cross-country cycling. Travelers will discover rural roads that meander along streams and past historic farmhouses. Before driving back to Boston, drop by the farmer’s market to stock up on fresh snacks.

Where to stay: The Woodstock Inn and Resort has 142 traditional rooms and suites that mix history (like handmade furniture) with modern amenities (think: Wi-Fi, Nespresso machines and flat-screen televisions). Located about nine miles from Woodstock in Barnard, Twin Farms is an exclusive five-star resort spread across 300 acres. The all-inclusive has a renowned culinary program — and a price tag to match.

What to eat and drink: With thousands of farms in the state of Vermont, food in the Green Mountain state is incredibly fresh. Worthy Kitchen, for example, has a rotating menu based on what’s in season, as well as a beer list that showcases some of the state’s finest craft breweries, including Hill Farmstead and the Alchemist. At Soulfully Good Cafe, visitors can try the signature cream apricot scones for a sweet breakfast on-the-go.

Narragansett, Rhode Island

Distance from Boston: 1.5 hours

This coastal Rhode Island town is a classic New England beach destination, with four of the state’s arguably most popular beaches nearby. Visitors will get their fill of local seafood while exploring the oceanfront, or venturing to nearby Block Island or Newport.

What to do: Situated on 60 acres of state parkland, The Scarborough State Beach boasts more than 2,000 feet of sandy ocean frontage and is home to a newly renovated pavilion. Narragansett Beach may be one of the best on the East Coast, and if lighthouses and history are your thing, visit the historic Port Judith Lighthouse, which was first constructed in 1806. The Towers, or Twin Towers, is another landmark structure, and it’s the only remnant of the Narragansett Pier Casino, which was the heart of Narragansett during the late 19th century. Today, the restored Towers typically host an assortment of events, including dance lessons and musical performances.

Where to stay: Many of the rooms at the Aqua Blue Hotel have full or partial ocean views (and balconies), and it's centrally located in town. There are also several bed and breakfasts, such as the Ocean Rose Inn, which overlooks Newport Harbor, Narragansett Bay and Jamestown Island. Eighteen new rooms were revealed in 2017 as part of a property renovation.

What to eat and drink: Built in the late 1800s by the U.S. Coast Guard, this granite structure is now home to the Coast Guard House, a seafood restaurant perched on Narragansett Bay. If you overslept, head to Crazy Burger (hear us out). In addition to an eclectic vegetarian-friendly menu with items like the Poco Loco Vegan Burger, the restaurant usually serves breakfast until 4 p.m. daily.

Additional reporting by Melanie Lieberman.

Featured image by Getty Images

Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.