New England’s big cities like Boston tend to steal the spotlight — and as someone who’s spent countless weekends exploring this corner of America, I get why people flock to these well-known spots. But when you’re dealing with packed streets, long restaurant waits, and tourist-filled attractions, it’s hard to feel like you’re actually getting away from it all.
Lucky for us, New England is packed with charming small towns, quiet coastal villages, and hidden mountain retreats that most tourists haven’t discovered yet. From Maine’s rocky shores to Vermont’s rolling hills, there’s so much more to experience beyond the usual destinations. Whether you’re craving a peaceful beach escape or a cozy mountain hideaway, I’ve put together a list of my favorite weekend spots that’ll help you see New England in a whole new light.
Newport, Rhode Island
My first visit to Newport was during the peak of summer, when this coastal gem truly comes alive. Perched along Rhode Island’s southern shores, Newport has been a playground for America’s elite since the Gilded Age. Grand mansions line the famous Cliff Walk, where you can stroll between sprawling estates and the deep blue Atlantic waters. The city’s downtown harbor area is packed with 18th-century buildings, upscale restaurants, and cozy boutiques, while Ocean Drive offers sweeping coastal views that have drawn visitors for generations. The Tennis Hall of Fame and annual jazz festival add layers of culture to this seaside retreat, but it’s the laid-back maritime atmosphere and fresh seafood that keep people coming back. Whether you’re sailing in the harbor or touring the opulent Vanderbilt summer “cottages,” Newport manages to blend historic charm with modern coastal living in a way few other New England towns can match.
Martha’s Vineyard, Massachusetts
Martha’s Vineyard first caught my eye during a quick summer escape in 2018. Just seven miles off the Massachusetts coast, this triangular island sits like a gem in the Atlantic Ocean, beckoning both day-trippers and seasonal residents. The island’s six towns each tell their own story – from Edgartown’s white-trimmed captain’s homes to the rainbow-colored gingerbread cottages in Oak Bluffs. Sandy beaches stretch along the 25-mile coastline, while inland, rolling farms and quiet forests create perfect cycling routes. The island’s western edge at Aquinnah showcases dramatic clay cliffs, where the historic lighthouse stands watch over the waves below.
Portland, Maine
A weekend in Portland first won me over back in 2018, when I discovered this seafaring city along Maine’s rugged Atlantic coast. Perched at the edge of Casco Bay, Portland stands as the state’s largest city, though it maintains the warmth of a close-knit coastal community. The cobblestone streets of the Old Port district wind past weathered brick buildings and working fishing wharves, where lobster boats still pull up with their daily catches. Local restaurants dot the waterfront, serving up fresh seafood and craft beer, while the Portland Head Light lighthouse keeps its century-old watch over the rocky shoreline. The city’s mix of maritime heritage and modern food scene makes it an ideal escape, especially when you can grab a window seat at Eventide Oyster Co. and watch fishing boats glide across the harbor at sunset.
Stowe, Vermont
I always tell outdoor enthusiasts to head straight to Stowe, Vermont. Nestled in the Green Mountains, this charming New England town offers year-round adventure with the Stowe Mountain Resort for skiing, the Recreation Path for biking, and countless hiking trails that wind through the surrounding forests. The downtown area, with its white church steeple and boutique shops, looks like it jumped straight off a postcard, while the nearby Ben & Jerry’s factory adds a sweet touch to any visit.
Bar Harbor, Maine
Explore the charming coastal town of Bar Harbor, where Acadia National Park meets the Atlantic Ocean. Take a guided kayak tour around the rocky shores to spot seals and puffins, or hike the park’s well-maintained trails for views of the rugged coastline. When hunger strikes, head to the walkable downtown area, where you can feast on fresh-caught lobster at waterfront restaurants or browse the locally-owned shops selling Maine-made goods. For a traditional New England experience, book a room at one of the historic inns overlooking Frenchman Bay, where you can watch sailboats glide by from your private porch.
The Berkshires, Massachusetts
The Berkshires remind me of what New England does best – mixing culture with countryside in the most natural way possible. This region in western Massachusetts draws both art lovers and outdoor enthusiasts, who come to hike the gentle mountains by day and catch world-class performances at Tanglewood by night. The area really shines in fall, when the maple trees put on their annual show and local farms welcome visitors for apple picking and hay rides. It’s not trying to be fancy – you’ll find plenty of down-to-earth diners serving pancakes with local maple syrup alongside the high-end restaurants and luxury spas. But that’s exactly what makes the Berkshires feel like such an authentic escape from city life.
Block Island, Rhode Island
Block Island sits just 13 miles off Rhode Island’s coast, but stepping onto its shores feels like entering a different era entirely. This peaceful island, reached by a quick ferry ride from Point Judith, is where New Englanders have been escaping the mainland hustle for generations. Its 17 miles of free public beaches wrap around the island like a ribbon, while two historic lighthouses stand guard over the rocky shores. You won’t find any chain stores or traffic lights here – just winding roads leading to hidden coves, conservation trails cutting through rolling meadows, and small shops housed in weathered gray-shingled buildings. It’s the kind of place where you can spend your mornings cycling past stone walls, your afternoons lounging on Crescent Beach, and your evenings sampling fresh seafood at family-owned restaurants that have been serving island visitors for decades.
White Mountains, New Hampshire
Adventure seekers flock to New Hampshire’s White Mountains for the region’s network of challenging hiking trails and outdoor activities, but the area offers much more than just mountain pursuits. The 800,000-acre White Mountain National Forest includes Mount Washington – the highest peak in the Northeast – along with 47 other notable summits that create perfect conditions for both summer hiking and winter skiing. In fall, the mountains burst into shades of red and gold, drawing leaf-peepers to scenic drives along the Kancamagus Highway. Throughout the year, small towns like North Conway and Lincoln welcome visitors with cozy inns, local restaurants, and family-friendly attractions like the Conway Scenic Railroad and Flume Gorge.
Cape Cod, Massachusetts
Escape to the sun-soaked shores of Cape Cod, where pristine beaches stretch for miles along the curved peninsula. Take your pick from charming seaside towns like Provincetown, Hyannis, or Chatham, each offering its own mix of fresh seafood spots and local boutiques. Bike the 22-mile Cape Cod Rail Trail through cranberry bogs and coastal villages, or hop aboard a whale watching tour to spot humpbacks breaching off the coast. For history buffs, the Kennedy family compound and numerous lighthouses offer a glimpse into New England’s maritime past. The evening clam bakes and sunset beach walks make this the ideal spot for a romantic summer escape.
Nantucket, Massachusetts
Ever wondered what it’s like to step into a postcard-perfect New England seaside town? That’s Nantucket for you, a small island 30 miles off the Massachusetts coast where cedar-shingled cottages line cobblestone streets and fishing boats bob in the harbor. Once the whaling capital of the world, this charming isle now draws visitors with its 82 miles of public beaches, historic lighthouses, and cranberry bogs that turn bright red come autumn. You can cycle along quiet paths to Siasconset Beach, learn about the island’s maritime history at the Whaling Museum, or join locals for fresh lobster rolls at Straight Wharf Fish Store – all while basking in that laid-back island atmosphere that makes Nantucket feel worlds away from mainland life.
Burlington, Vermont
Many visitors flock to Burlington for Lake Champlain’s beautiful shoreline, but this college town offers much more than waterfront views. The Church Street Marketplace, a car-free downtown area, serves as the city’s social hub with local shops, cafes, and street performers creating a welcoming atmosphere. In summer, the Burlington Farmers Market brings together local farmers, artisans, and food vendors, while the surrounding Champlain Valley provides excellent spots for hiking and biking. Though the city comes alive during warm months, winter transforms Burlington into a gateway for nearby ski resorts, proving there’s no wrong time to visit this friendly Vermont destination.
Portsmouth, New Hampshire
Ever walked down streets where sea captains once lived in grand mansions? That’s everyday life in Portsmouth, where colonial history meets modern New England charm. This coastal gem, just an hour north of Boston, lets you hop between cozy coffee shops housed in buildings from the 1700s and browse indie bookstores tucked into historic brick lanes. Take a stroll through Prescott Park to watch boats drift by in the harbor, or catch a show at The Music Hall, one of the oldest operating theaters in America. The food scene here punches well above its weight – think fresh lobster rolls served in centuries-old taverns and craft breweries set in restored warehouses along the waterfront.
Acadia National Park, Maine
Perched on the rugged coast of Maine, Acadia National Park has always held a special place in my heart. This 47,000-acre park is where New England’s rocky shoreline meets dense forests and smooth-sided mountains, creating a landscape that feels distinctly different from other national parks. It’s a place where you can watch the sunrise from Cadillac Mountain (the first spot in the U.S. to see dawn), bike along historic carriage roads, or spend hours exploring tide pools along the granite-lined shore. While summer draws the biggest crowds, I’ve found that autumn brings a special magic – the cooler temperatures perfect for hiking, and the maple trees putting on their annual show of reds and golds. The park isn’t just about nature though; the charming town of Bar Harbor sits right at its doorstep, offering the perfect base for your adventures.
Mystic, Connecticut
Just 90 minutes from Boston sits the charming maritime town of Mystic, Connecticut. Like many New England coastal communities, Mystic has its share of seafood shacks, boat-filled harbors, and nautical history. But unlike the others, it feels like stepping into a living maritime museum. Watch the historic drawbridge rise and fall as sailboats glide underneath, and you’ll understand what I mean. Because of Mystic’s rich shipbuilding past and the presence of America’s largest maritime museum, the town has preserved its seafaring culture remarkably well, and you’ll find colonial-era homes, weathered captain’s houses, and one of the country’s oldest surviving commercial ships dotting the waterfront.
Woodstock, Vermont
Ever seen a maple tree tap dripping sweet sap into a metal bucket? That’s an everyday scene in Woodstock, Vermont, where classic New England charm meets pure country comfort. This picture-perfect town, nestled in the Green Mountains, serves up the best of rural Vermont life – from locally-made cheese at Sugarbush Farm to covered bridges that look like they belong on a postcard. The Billings Farm & Museum lets you step back in time to experience authentic 1890s farm life, while the downtown area, with its brick sidewalks and family-owned shops, feels like walking through a Norman Rockwell painting. When winter rolls in, the nearby Suicide Six ski area offers cozy slopes perfect for families, and the Woodstock Inn’s roaring fireplaces make ideal spots for warming up with hot cocoa.
North Conway, New Hampshire
Ever watched the Conway Scenic Railroad wind through snow-capped mountains while sipping hot chocolate? That’s just another winter morning in North Conway, a charming mountain town tucked into New Hampshire’s Mount Washington Valley. This outdoor playground draws visitors year-round with its mix of activities – from skiing at Cranmore Mountain Resort to hiking the White Mountain National Forest trails. The town’s Main Street looks like it jumped straight out of a Norman Rockwell painting, with its red-brick buildings housing local shops and cozy cafes. At Settlers Green, you’ll find over 60 outlet stores offering tax-free shopping, while Diana’s Baths waterfall offers a peaceful forest retreat just minutes from downtown.
Provincetown, Massachusetts
Step into the lively spirit of Provincetown, where colorful art galleries line Commercial Street and beach vibes mix with New England charm at the tip of Cape Cod. You can hop on a whale watching cruise from MacMillan Pier to spot humpbacks breaching in their natural habitat, or rent a bike to explore the winding trails of the Province Lands. Head to Race Point Beach for a peaceful afternoon of sunbathing and seal-spotting, or climb the 252-foot Pilgrim Monument for views that stretch across the entire cape. When evening comes, grab fresh seafood at one of the local spots along the harbor, then catch a cabaret show at one of P-town’s famous performance venues.
Watch Hill, Rhode Island
Many travelers head to Watch Hill for its classic New England charm and the seaside lifestyle, but this coastal village offers more than just beach views. The area features the historic Flying Horse Carousel – the oldest operating carousel of its kind in America – along with quiet streets lined with independent shops and seafood restaurants. In summer, visitors can stroll along the pristine beaches, take sailing lessons in the harbor, or explore the Watch Hill Lighthouse that’s stood guard since 1856. While the warmer months draw the biggest crowds, Watch Hill’s small-town atmosphere and coastal walks make it worth visiting in any season.
Kennebunkport, Maine
Nestled along Maine’s rocky coastline, Kennebunkport first caught my eye during a summer road trip in 2018. This former shipbuilding village has evolved into one of New England’s most charming coastal escapes, where weathered fishing boats bob alongside glossy yachts in the harbor. Cozy bed-and-breakfasts and classic New England cottages line the winding streets of Dock Square, while the famous Bush family compound sits regally on Walker’s Point. The town comes alive in summer when visitors flock to Goose Rocks Beach for lazy days by the Atlantic, but I particularly love exploring the quiet coves and local lobster shacks during the peaceful shoulder season. Ocean Avenue’s scenic drive offers perfect views of the crashing waves, while the hidden gem of Cape Porpoise Harbor gives you a glimpse of authentic Maine fishing life.
Lake Winnipesaukee, New Hampshire
Lake Winnipesaukee has been New Hampshire’s premier lake destination since I first visited as a kid in the 1990s. The largest lake in the state, Winnipesaukee stretches across 72 square miles of crystal-clear water, dotted with 258 islands and bordered by eight different towns. Charming lakeside communities like Wolfeboro and Meredith line its 288-mile shoreline, offering everything from kayak rentals to ice cream shops. The historic M/S Mount Washington cruise ship has been a fixture on these waters since 1872, taking visitors on scenic tours past waterfront mansions and quiet coves. When fall arrives, the surrounding mountains put on a show of red and gold that reflects perfectly in the lake’s mirror-like surface.