5 Fun Escapes Around New England to Make this Fall

A sunset view along the Mohawk Trail in the Berkshires. Photograph by Wolf Mathewson

Fun fall getaways are just a drive away to the Berkshires, the Cape, Sunapee, the seacoast of New Hampshire and southern Vermont. By Lauren Clem, Jamie Coelho, Dana Laverty, Kaitlyn Murray and Kerri Tallman 

INDEX

The Berkshires, MA | Chatham, MA | Portsmouth, NH | Southern Vermont | Sunapee, NH

The Berkshires,  Massachusetts

Best known as the summer home of the Boston Symphony Orchestra and world-class art museums, this quiet corner of New England is a foodie and art-lover’s paradise in any season. By Lauren Clem

Downtown Lee, Massachusetts. Photograph via Getty Images/H Stiver.

Two hours away lies a delightful paradox, a rural retreat where you can enjoy top-notch dining, museums, shopping and performances that best even the big city. Don’t believe us? Just hop on the Mass Pike and experience it for yourself. 

SATURDAY AFTERNOON: A midmorning start gets us to the heart of the Berkshires by lunchtime, including a few extra minutes to sleep in that somehow feel like cheating. The cluster of small towns on either side of Interstate 90 offers up endless versions of small-town Americana with an upscale twist, and we start our journey in Lee to take advantage of the weekly Lee Farmers Market (Saturdays through Oct. 7, leefarmersmarket.com). After stocking up on rhubarb cookies and local honey, we wander into the Starving Artist Cafe and Creperie (starvingartistcreperie.com), where crepes come loaded with everything from marinated tempeh to salsa and sour cream. My boyfriend devours the chicken and prosciutto special with goat cheese and arugula, while I opt for a lighter apple beet salad to save room for the well-stuffed peanut butter and banana crepe topped with whipped cream for dessert. 

Fall foliage in the Berkshires. Photograph via Getty Images/Dennis Tangney Jr.

After lunch, we drive through picturesque downtown Stockbridge and arrive at the Norman Rockwell Museum (nrm.org). The artist spent the last twenty-five years of his life in Stockbridge, working out of a cottage-like studio that now sits on the museum grounds. The town’s charming characters are captured in the Saturday Evening Post covers in the museum’s lower level, but it’s the more serious works upstairs that leave us reeling with their depiction of a racially divided community in the wake of World War II. 

The Norman Rockwell Museum. Photograph courtesy of Massachusetts Office of Travel and Tourism.

SATURDAY EVENING: We check into our lodging for the evening, the beautifully appointed Cornell Inn (cornellbb.com) in Lenox. Kurt Inderbitzin and Indrani Pillai purchased the inn in 2021, trading in their careers in the global entertainment business for a philosophy of kindness in the Berkshire hills. The approach shines through in everything from the boutique rooms — individually designed by twenty-three BIPOC designers — to the complimentary welcome drinks and brownies. We set our bags down in the Lioness — a desert-hued room with safari vibes — and within minutes, we’re sipping peach sangria in the airy bar that doubles as a puzzle room. For dinner, we head to Firefly Gastropub (fireflylenox.com), whose farmhouse-style porch gives way to a buzzy interior featuring mood-lit booths surrounding a central bar. An enormous plate of Brussels sprouts with Parmesan blue cheese butter and a demi baguette almost fill us up, but we manage to find room for the panko-and-pistachio-encrusted trout and airline chicken. Loaded up on carbs, we drag ourselves back to the hotel, where more brownies (they’re impossible to resist) and a cognac nightcap await. 

The Lakehouse Inn. Courtesy of Lakehouse Inn

SUNDAY MORNING: The morning begins with the scent of coffee and breakfast drifting over from the main house. The inn serves an exceptional complimentary breakfast, and my boyfriend awards high marks to the egg frittata with goat cheese, red peppers and baby spinach. Still stuffed from the previous night’s culinary excursions, I pass on the Belgian waffle and instead enjoy a simple side of toast with orange marmalade and cinnamon sugar. 

After checking out, we pass the morning and early afternoon perusing the shops in downtown Lenox. While art enthusiasts and fashionistas will revel in the galleries and boutiques lining Church Street, the town has options for all budgets and tastes. The Bookstore (bookstoreinlenox.com) is a literary lover’s paradise — for some booze with your books, check out the adjoining Get Lit Wine Bar — while the aptly named Catwalk Boutique (catwalkboutique.org) benefits the local humane society with its well-curated thrift selection. We ogle the beautiful cashmere throws at MacKimmie Co. (mackimmieco.com) before hitting up What A Gift (whatagiftlenox.com) for its quirky selection of local goodies. 

SUNDAY AFTERNOON: Between shopping sprees, we grab brunch at Haven (havencafebakery.com), a hub for bakery items and home-cooked fare. The huevos rancheros come loaded with avocado, salsa and spicy black beans, and a steaming bowl of steel-cut oats topped with homemade granola casts the breakfast standby in a whole new light. Even the baked goods are irresistible, and we grab a morning glory muffin to go before skipping town for our next venture. 

The Boston Symphony Orchestra is back in the city, but we stop into Tanglewood anyway to walk the grounds of the storied music venue (open year-round to visitors outside of concert hours, bso.org/tanglewood).

The Koussevitzky Music Shed at Tanglewood. Courtesy of BSO Press Office/Fred Collins.

A brief drive through winding farmland brings us to Hilltop Orchards (hilltoporchards.com), a one-stop shop for fall frolicking with apple picking, cider doughnuts, hiking trails and an onsite winery and cidery. We sample the JMASH cider collection and leave with a bottle of Furnace Brook Winery chardonnay. 

Cider tasting at Hilltop Orchards. Photo by Lauren Clem.

SUNDAY EVENING: We check into our second night’s accommodation, the Lakehouse Inn (lakehouseinnlee.com) in Lee. Purchased by Inderbitzin and Pillai last year, the Lakehouse offers the same amenities as the Cornell at a serene waterfront property with a clean white interior and wraparound porch. We drop our bags and grab a quick dinner of grilled chicken and steak Terranova at Barrington Brewery and Restaurant (barringtonbrewery.net) in Great Barrington. I take a four-pack of the Barrington Brown to go and note the après-ski-style bar would be perfect on a chilly fall night. 

The Lioness Room at the Cornell Inn. Courtesy of the Cornell Inn.

A storm breaks as we head back toward Lenox, threatening our outdoor performance at the award-winning Shakespeare & Company (shakespeare.org). The setting sun emerges just in time to create a stunning backdrop to the Roman Garden Theatre, one of several venues the company maintains on a former boarding school campus just outside of town. After the show, we spend a few minutes back at the inn enjoying the sounds of the lake before turning in for the night. 

The Roman Garden Theatre at Shakespeare & Company.

MONDAY MORNING: A lazy morning gives us plenty of time to explore the property, including the kayaks down on the lake. Beginning this past July, the Lakehouse is home to Oasis Bar and Grill (lakehouseinnlee.com/oasis-bar-grill), an outdoor dining experience featuring live local musicians on a clifftop patio overlooking Laurel Lake. The restaurant isn’t open during our stay, but we preview the patio during a leisurely outdoor breakfast. This time, I indulge with abandon, nibbling at the warm pastry basket and digging into fluffy French toast served with bacon, fruit and five-spiced potatoes. We reluctantly pull ourselves away from the view and pack up our things before heading south out of town. 

MONDAY AFTERNOON: Passing through Great Barrington, we grab lunch at the Great Barrington Bagel Company and Deli (gbbagel.com), a classic New York-style bagel joint featuring matzo ball soup and all the spreads you could possibly want. A half-hour drive south, Bash Bish Falls State Park (mass.gov/locations/bash-bish-falls-state-park) beckons with its pristine views and thundering waterfall. We skip the steep hike from the Massachusetts side and instead park on the New York side of the falls, where a gentle incline climbs beside a brook. Though access to the falls themselves has been closed since 2022, you can still enjoy the view from an overlook. Save some Instagram shots for the ride home, when the Berkshires scenery unfolds in miles of pastoral bliss all the way back to I-90. 

Bash Bish Falls State Park. Photo courtesy of Massachusetts Office of Travel and Tourism.

NUTS & BOLTS 

Travel time: Two hours from Providence. 

Miles: 120 miles. 

How to Get There: I-90 West. 

Best Season to Go: Year-round. Fall is great for leaf-peeping, while winter has ski resorts and summer brings the Boston Symphony Orchestra and Jacob’s Pillow Dance Festival. 

Bucket List for Next Time: The Mount, former home of Edith Wharton. The author and her husband built the estate in 1902 after tiring of their previous Newport abode. 

Worth a Detour: Williamstown and North Adams, home to even more art museums. The Clark Art Institute’s extensive collection dates back to the Renaissance, while MASS MoCA is a hub for contemporary art.  

Jacob’s Pillow. Photograph courtesy of Massachusetts Office of Travel and Tourism.

INDEX

The Berkshires, MA | Chatham, MA | Portsmouth, NH | Southern Vermont | Sunapee, NH