New England offers a remarkable variety of weekend getaways perfect for refreshing escapes within a few days. Whether you seek coastal charm, mountain adventures, cultural enrichment, or food-focused relaxation, this compact region delivers accessible towns and scenic retreats ideal for 2-4 day trips. Drive times from central Massachusetts generally range from just over an hour to about four hours, making these towns perfect for weekend escapes without the hassle of long-haul travel.

These destinations vary in walkability, from highly walkable downtowns filled with boutiques and cafes to scenic coastal drives and mountain villages that require a car. Many cater to couples, families, friends, or solo travelers, each with a distinct vibe ranging from luxury resorts to historic inns and boutique hotels. This guide sorts the best weekend getaways in New England by proximity, illustrating why each town works for specific interests and travel styles, with detailed hotel, dining, and activity suggestions, along with insider advice.

Quick Overview: Best Weekend Getaways in New England, USA

• Portsmouth, New Hampshire
• Mystic, Connecticut
• Newport, Rhode Island
• The Berkshires (Lenox/Stockbridge), Massachusetts
• Kennebunkport, Maine
• Portland, Maine
• North Conway, New Hampshire
• Provincetown, Massachusetts
• Stowe, Vermont
• Burlington, Vermont

Portsmouth, NH

Portsmouth is a historic New England seaport renowned for its compact, highly walkable downtown with brick-lined streets rich in culture and culinary delights. Ideal for couples, friends, and solo travelers, Portsmouth offers a cultural, food-focused, and relaxing weekend where everything is within reach on foot. The blend of history, excellent dining spots, and waterfront charm makes it an enriching short trip.

Best Hotels to Stay in Portsmouth

• Hotel Portsmouth: A boutique hotel set in a beautifully restored 1881 Queen Anne Victorian mansion offering stylish intimacy close to Market Square—perfect for romantic getaways.
• Wentworth by the Sea: A grand luxury historic hotel outside downtown with Gilded Age grandeur and spa amenities, ideal for special occasions or romantic splurges.
• The Sailmaker's House: A boutique inn with only 10 rooms in a historic home, offering charm and quiet coziness right in the heart of downtown yet on a peaceful side street.

Best Restaurants to Try in Portsmouth

• Cure: Casual but sophisticated American comfort food; try the Cure Burger or Duck Confit Poutine, paired with excellent cocktails.
• Moxy: Modern American tapas with a lively atmosphere; share the Beef Short Rib Marmalade and Fried Whole Belly Clams.
• Row 34: Sleek seafood and oyster bar serving local oysters and Ethel’s Creamy Lobster Roll; a splurge worthy of seafood lovers.

Best Things to Do in Portsmouth

• Strawbery Banke Museum: Step back in time at this outdoor history museum with historic homes and costumed interpreters illuminating four centuries of local life.
• Explore Market Square: Soak in the lively heart of Portsmouth with galleries, shops, and cafes for a culturally rich afternoon stroll.
• Prescott Park: Enjoy scenic waterfront flower gardens and walking paths, especially vibrant during the summer arts festival season.

2-Day Itinerary in Portsmouth

• Day 1: Check in and explore Market Square’s shops and cafes. Indulge in pre-dinner drinks at The Wilder, then enjoy a tapas-style dinner at Moxy.
• Day 2: Visit Strawbery Banke Museum in the morning, then relax with a stroll through Prescott Park. Finish with a late seafood lunch at Row 34 before departing.

Insider Local Tips

• For a view of the iconic tugboats, enjoy late afternoon drinks on Bow Street decks to avoid evening crowds.
• Avoid parking frustration by using Hanover Street Parking Garage, which is centrally located with available spaces and reasonable rates.
• Portsmouth attracts many weddings; book lodging and popular restaurants a month or two in advance for summer and fall weekends.
• Coffee lovers should try Cup of Joe or Popovers on the Square for a true local morning experience.

Best Time to Visit Portsmouth

Summer and Fall offer the best weather, vibrant festivals, and ideal outdoor conditions for walking and dining.

Mystic, CT

Mystic blends maritime history and modern charm within a medium walkability setting, making it excellent for families and couples who want cultural enrichment with engaging activities and good food. This historic seaport town features a world-class aquarium and seaport museum alongside a walkable downtown with waterfront views.

Best Hotels to Stay in Mystic

• Spicer Mansion: Luxurious Relais & Châteaux property with personalized service, ideal for a romantic splurge with exceptional detail and ambiance.
• The Whaler's Inn: Historic inn right downtown adjacent to the Bascule Bridge, offering unbeatable access to Mystic's core.
• Hyatt Place Mystic: Modern, budget-friendly hotel located in Olde Mistick Village, practical for families seeking proximity to key attractions.

Best Restaurants to Try in Mystic

• Oyster Club: Upscale seafood with a boat-to-table philosophy; order the daily raw oysters and the Butcher’s Burger at the Treehouse bar.
• S&P Oyster Restaurant and Bar: Waterfront dining with South American-inspired seafood; don’t miss the Clam Chowder and Pan Seared Sea Scallops.
• Mystic Pizza: Casual, iconic pizzeria famed for its classic cheese pizza and movie memorabilia—a fun family stop.

Best Things to Do in Mystic

• Mystic Seaport Museum: America's leading maritime museum with an extensive 19th-century village and historic vessels like the Charles W. Morgan.
• Mystic Aquarium: Home to beluga whales and diverse marine life, offering engaging indoor and outdoor exhibits.
• Downtown Mystic & Bascule Bridge: Explore shops, cross the hourly-opening drawbridge, and enjoy river views.

2-Day Itinerary in Mystic

• Day 1: Check in and visit the Mystic Seaport Museum (allocate at least 3-4 hours). Dinner at S&P Oyster with waterfront views.
• Day 2: Morning at Mystic Aquarium with beluga and sea lion shows. Grab a slice at Mystic Pizza for lunch, then explore Olde Mistick Village shops.

Insider Local Tips

• The Mystic Bascule Bridge opens hourly, stopping foot and car traffic briefly—time your crossings accordingly.
• Venture 10 minutes to Stonington Borough to avoid main attraction crowds and discover coastal charm.
• Reserve Oyster Club dining a month in advance, but try for outdoor Treehouse walk-ins.
• Sift Bake Shop’s morning baked goods sell out fast—order online to skip the line.

Best Time to Visit Mystic

Summer and Fall best suit Mystic’s outdoor and family-friendly offerings with pleasant weather and lively events.

Newport, RI

Newport is synonymous with Gilded Age opulence and America's First Resort status, combining luxury, rich cultural experiences, and coastal beauty. Its medium walkability is ideal for couples, friends, and families looking for a mix of mansion tours, scenic coastal walks, and waterfront dining with a refined yet relaxed atmosphere.

Best Hotels to Stay in Newport

• The Chanler at Cliff Walk: A luxury boutique mansion hotel on the famous Cliff Walk with ocean views, historic grandeur, and top-notch service.
• Castle Hill Inn: A secluded luxury resort on a private peninsula featuring a private beach and iconic sunset lawn views.
• The Brenton Hotel: Modern luxury on the harbor with nautical-themed rooms and a rooftop bar, convenient for downtown exploration.

Best Restaurants to Try in Newport

• The Clarke Cooke House: Classic American seafood with harbor views; try the ‘Snowball in Hell’ dessert and dine on the Porch or SkyBar.
• Giusto: Modern Italian with a lively atmosphere and harbor vistas; order the Mafaldine with Clam Sauce and a Negroni.
• The Black Pearl: Iconic clam chowder spot with both a formal dining room and casual patio on Bannister’s Wharf.

Best Things to Do in Newport

• The Cliff Walk: A scenic 3.5-mile trail combining shoreline views and historic Gilded Age mansions, especially between The Breakers and Ochre Court.
• Tour The Breakers Mansion: Explore the Vanderbilt summer “cottage,” an opulent oceanfront estate representing Newport’s high society.
• Drive the Ocean Drive: A 10-mile scenic route along Aquidneck Island’s coast featuring ocean vistas and historic forts.

2-Day Itinerary in Newport

• Day 1: Arrive and walk the northern Cliff Walk from Easton’s Beach. Evening on Thames Street with dinner at The Black Pearl.
• Day 2: Morning tour of The Breakers, followed by a scenic Ocean Drive. Enjoy late lunch and cocktails at Castle Hill Inn lawn for iconic views.

Insider Local Tips

• Avoid morning traffic over the Pell Bridge on summer weekends by arriving before 10 AM or after 3 PM.
• Skip downtown parking headaches by using the Newport Visitor Center lot on America’s Cup Ave, then walk.
• Book summer weekend hotels 6-9 months ahead and dinner reservations a month or more in advance.
• For fewer crowds and better waves, locals recommend Second Beach (Sachuest Beach) in nearby Middletown.

Best Time to Visit Newport

Summer is the top season for Newport’s mansion tours, beach walks, and sailing culture.

The Berkshires, MA

The Berkshires epitomize a cultural and natural New England retreat with rolling hills, world-class art institutions, and refined dining amid rural charm. Ideal for couples, solo travelers, and outdoor lovers seeking a luxury or relaxing cultural escape, the area invites leisurely drives and outdoor exploration. The walkability is low, so expect to rely on a car.

Best Hotels to Stay in The Berkshires

• Blantyre: Luxury resort and historic mansion surrounded by stunning grounds, perfect for a European country estate experience.
• The Red Lion Inn: A historic inn since 1773 in Stockbridge, known for its classic New England charm and a welcoming front porch.
• Miraval Berkshires Resort & Spa: All-inclusive wellness spa retreat designed for mindfulness and total relaxation.

Best Restaurants to Try in The Berkshires

• The Prairie Whale: Casual farm-to-table comfort food with a cozy backyard patio and lively atmosphere.
• Cafe Triskele: Intimate French bistro serving perfect classics like Steak Frites and Duck Confit.
• Once Upon a Table: Romantic, intimate bistro tucked away in Stockbridge offering refined American dishes like Pan-Seared Scallops.

Best Things to Do in The Berkshires

• Tanglewood: Enjoy world-class summer concerts on the lawn with a picnic in hand, home of the Boston Symphony Orchestra.
• The Clark Art Institute: Explore a renowned art museum with European masterpieces and modern architecture surrounded by walking trails.
• Hike Monument Mountain: A moderate 3-mile loop with panoramic views and a connection to literary history.

2-Day Itinerary in The Berkshires

• Day 1: Check into your inn; visit Stockbridge and the Norman Rockwell Museum. Dinner at The Red Lion Inn.
• Day 2: Morning hike up Monument Mountain, afternoon at The Clark Art Institute, then an evening picnic concert at Tanglewood (summer only).

Insider Local Tips

• Arrive early for Tanglewood lawn concerts (1.5-2 hours ahead) to secure a good spot.
• Plan driving routes thoughtfully since roads between towns can be slow and winding.
• Reserve lodging and dinners 6+ months ahead for summer concert season—tickets also sell out quickly.
• Shop the Great Barrington Farmers Market Saturday mornings and try local sandwiches at Lenox B-T-R.

Best Time to Visit The Berkshires

Summer and Fall magnify cultural and scenic appeal with concerts and foliage.

Kennebunkport, ME

Kennebunkport epitomizes classic Maine coastal charm with sandy beaches, rugged seaside beauty, and a historic town center centered on Dock Square. Suited for couples and families seeking a relaxing, luxury-focused, and food-rich weekend, it combines upscale comfort with authentic New England seaside experiences in a moderately walkable downtown.

Best Hotels to Stay in Kennebunkport

• Hidden Pond: Luxury cottage resort set in birch forests with pools and a treetop spa—perfect for a romantic splurge or serene retreat.
• White Barn Inn, Auberge Resorts Collection: Renowned for its fine dining and elegant rooms, this spa inn epitomizes luxurious New England hospitality.
• The Boathouse Waterfront Hotel: Nautical-themed boutique hotel on the river, ideal for those wanting to be in the heart of the action with waterfront views.

Best Restaurants to Try in Kennebunkport

• The Clam Shack: Legendary seafood shack famous for lobster rolls on a round bun and fried clams—casual and iconic.
• Earth at Hidden Pond: Romantic, farm-fresh tasting menus in a rustic barn setting with herbal cocktails from the garden.
• Mabel's Lobster Claw: Traditional, family-friendly seafood with no-frills lobster dinners popular for decades.

Best Things to Do in Kennebunkport

• Explore Dock Square: Browse art galleries, boutiques, and waterfront spots in the bustling town center.
• Goose Rocks Beach: A serene, three-mile stretch of protected sandy beach perfect for families.
• Walk along Ocean Avenue: Scenic stroll or drive past historic homes and the Bush family compound with iconic coastal views.

2-Day Itinerary in Kennebunkport

• Day 1: Arrive and stroll Dock Square. Lunch at The Clam Shack, afternoon at Gooch’s Beach, and dinner at The Boathouse.
• Day 2: Morning at Goose Rocks Beach (parking pass required), scenic drive along Ocean Avenue, and splurge dinner at Earth at Hidden Pond.

Insider Local Tips

• Summer weekend traffic can be heavy; arrive early and park once to explore on foot or use the local trolley.
• Parking passes are mandatory for Goose Rocks Beach; buy them early at local stores or town hall.
• Book highly desired hotels and restaurants 3-12 months in advance for summer.
• For a less crowded lobster experience, try Nunan’s Lobster Hut in nearby Cape Porpoise.

Best Time to Visit Kennebunkport

Summer is prime season for beaches, boating, and outdoor dining.

Portland, ME

Portland combines historic coastal charm, a nationally renowned food scene, and a vibrant arts district within a compact, highly walkable footprint. Perfect for couples, friends, and solo travelers seeking a food-focused, cultural, and relaxing trip. Its cobblestone Old Port streets, working waterfront, and accessible arts scene create an engaging, easy-paced urban escape.

Best Hotels to Stay in Portland

• The Press Hotel, Autograph Collection: A luxury boutique hotel in the former newspaper building with journalistic decor, an art gallery, and upscale dining—ideal for romantic and cultural stays.
• Portland Harbor Hotel: A luxury hotel with Old Port centrality, a garden courtyard, a fire pit, and complimentary bike rentals offering waterfront calm near the city buzz.
• The Francis: Boutique hotel in a restored historic mansion, perfect for quieter, architecturally rich West End exploration.

Best Restaurants to Try in Portland

• Eventide Oyster Co.: James Beard Award-winning modern oyster bar; try the Brown Butter Lobster Roll and local oysters.
• Duckfat: Casual Belgian-inspired spot famed for duck fat fries and Duck Confit Panini—budget-friendly comfort food favorite.
• Fore Street Restaurant: Pioneer wood-fired farm-to-table restaurant with standout roasted pork loin and mussels, perfect for a romantic splurge.

Best Things to Do in Portland

• Explore the Old Port: Historic district with cobblestones, boutiques, galleries, and vibrant working waterfront sights.
• Visit Portland Head Light: Maine’s oldest iconic lighthouse with cliffside ocean views at Fort Williams Park.
• Ferry to Peaks Island: Short ferry ride to a charming island ideal for biking or golf cart tours along scenic loops.

2-Day Itinerary in Portland

• Day 1: Arrive and wander Old Port’s cobblestone streets. Early dinner at Eventide Oyster Co., followed by craft cocktails at Blyth & Burrows.
• Day 2: Morning coffee and donuts at The Holy Donut, photos at Portland Head Light, lunch at Duckfat, then an afternoon exploring the Arts District or Peaks Island.

Insider Local Tips

• Off-peak dining times for popular spots like Eventide minimize long lines; try 3 PM weekdays.
• Don’t limit exploration to Old Port—West End has stunning Victorian homes; East End offers breweries and harbor views.
• Fore Street dinner reservations require exact 60-day booking in advance; popular hotels fill quickly for summer/fall weekends.
• Locals recommend Highroller Lobster Co. for creative, less crowded lobster rolls.

Best Time to Visit Portland

Summer and Fall offer the best atmosphere for outdoor dining, island trips, and cultural events.

North Conway, NH

North Conway is the gateway to the White Mountains and a budget-friendly, family- and outdoors-focused base for all-season adventures. Though walkability is low, it features an active village center with outlet shopping, nearby scenic drives, and accessible hiking. It suits families, friends, and outdoor enthusiasts for budget-conscious nature and adventure escapes.

Best Hotels to Stay in North Conway

• Stonehurst Manor: Historic mansion on a hill with mountain views and cozy fireplaces; perfect for a romantic, old-world feel.
• Adventure Suites: Quirky, themed hotel with unique suites (Treehouse, Disco, Cave), great for families or couples seeking something fun and memorable.
• Eastern Slope Inn Resort: Historic resort with indoor pool and central location in the village, offering variety and convenience.

Best Restaurants to Try in North Conway

• Moat Mountain Smokehouse & Brewing Co.: Casual and lively BBQ and craft brewery serving solid pulled pork and house beers, great post-hike.
• Flatbread Company: Family-friendly spot renowned for organic, wood-fired pizzas in a rustic barn setting.
• Zeb's General Store: Not a restaurant but a must-stop for New England specialty foods, penny candy, and local condiments.

Best Things to Do in North Conway

• Drive the Kancamagus Highway: A 34.5-mile scenic byway famed for fall foliage, with overlooks and trailheads en route.
• Conway Scenic Railroad: Vintage train rides through the Mount Washington Valley with spectacular views, especially to Crawford Notch.
• Hike to Diana's Baths: Easy 1.3-mile hike to refreshing cascading pools popular with families.

2-Day Itinerary in North Conway

• Day 1: Arrive, shop Settlers Green Outlet Village, hike to Diana’s Baths, and dinner and local brews at Moat Mountain Smokehouse.
• Day 2: Morning drive on Kancamagus Highway with stops, afternoon scenic railroad ride, and farewell pizza at Flatbread Company.

Insider Local Tips

• For peak foliage, visit the Kancamagus on weekdays or start early weekend mornings to avoid traffic.
• Use West Side Road parallel to Route 16 to avoid congested main drag traffic.
• Book lodging 6-8 months in advance for fall weekends with high demand and premium pricing.
• For a quieter, picturesque drive, try Bear Notch Road connecting the Kancamagus to Bartlett.

Best Time to Visit North Conway

Fall stands out for breathtaking foliage and outdoor activity with moderate crowd control advice.

Provincetown, MA

Located at Cape Cod’s tip, Provincetown—or P-town—is a culturally vibrant, famously LGBTQ+-friendly town known for its lively arts scene, beautiful beaches, and walkable downtown. Perfect for couples, friends, and solo travelers seeking a food-focused, cultural, and relaxing getaway with a social atmosphere and beach access.

Best Hotels to Stay in Provincetown

• Salt House Inn: Stylish boutique inn known for minimalist design and homemade breakfast, a peaceful retreat near lively Commercial Street.
• Lands End Inn: Historic hilltop inn with panoramic harbor views and antique-filled rooms, excellent for romance.
• AWOL: Modern, social hotel with a pool and fire pits, offering a relaxed atmosphere in the West End.

Best Restaurants to Try in Provincetown

• The Lobster Pot: Classic seafood with signature Lobster Bisque and boiled lobster; upstairs dining offers harbor vistas.
• Canteen: Trendy modern seafood shack with a large backyard leading to the beach; don’t miss the Hot Lobster Roll and frosé.
• Strangers & Saints: Cozy Mediterranean tapas in a former captain’s home with inventive dishes and craft cocktails.

Best Things to Do in Provincetown

• Stroll Commercial Street: Busy main street with galleries, shops, bars, and vibrant people-watching.
• Race Point Beach: Wide, dune-backed beach with seal and whale spotting opportunities.
• Climb the Pilgrim Monument: Tall granite structure providing breathtaking 360-degree views of town and harbor.

2-Day Itinerary in Provincetown

• Day 1: Arrive and explore Commercial Street galleries and shops, followed by sunset drinks and dinner at Canteen.
• Day 2: Rent bikes to hit the Province Lands Bike Trail and Race Point Beach, then climb Pilgrim Monument. Dine at The Lobster Pot.

Insider Local Tips

• Commercial Street’s “Tea Dance” at the Boatslip (4 PM daily in summer) is the best time for people-watching.
• Avoid driving if possible due to heavy traffic and scarce parking; take Boston’s fast ferry instead.
• Book accommodations, ferry tickets, and show tickets far in advance for summer, especially around themed weeks.
• For quieter harbor access, explore West End side streets and don’t miss Portuguese Bakery’s traditional pastries.

Best Time to Visit Provincetown

Summer is the peak time for beach, nightlife, and arts festivals.

Stowe, VT

Nestled beneath Vermont’s highest peak, Stowe is a quintessential New England mountain town offering year-round adventure and luxury with a relaxed vibe. Perfect for outdoors enthusiasts, couples, and families, it balances high-end resorts with approachable activities like hikes, biking, brewery visits, and skiing. Walkability is low, so a car is necessary for exploring.

Best Hotels to Stay in Stowe

• Topnotch Resort: Luxury resort with indoor/outdoor pools, a spa, and family-friendly amenities.
• The Lodge at Spruce Peak: Ski-in/ski-out luxury hotel with restaurants, shops, and an ice rink within a self-contained village.
• Field Guide Lodge: Modern boutique hotel with cozy rooms, a heated pool, and a hot tub perfect after outdoor pursuits.

Best Restaurants to Try in Stowe

• The Alchemist Brewery: Home of the legendary Heady Topper IPA, offering samples and retail to-go beer.
• Doc Ponds: Casual gastropub known for elevated comfort food and an extensive beer list; try the Crafty Burger.
• Piecasso: Family-friendly pizzeria with wood-fired pizzas and an arcade, great after hiking or skiing.

Best Things to Do in Stowe

• Stowe Recreation Path: Scenic 5.3-mile paved greenway along the West Branch River, ideal for walking and biking.
• Drive Mount Mansfield Auto Toll Road / Gondola: Scenic drive or gondola ride offering 360-degree mountain views and access to Cliff House Restaurant.
• Hike to Moss Glen Falls: Easy, family-friendly short hike to a beautiful waterfall and swimming spot.

2-Day Itinerary in Stowe

• Day 1: Check in and walk or bike a section of Stowe Recreation Path; afternoon brewery stop at The Alchemist and dinner at Doc Ponds.
• Day 2: Morning scenic drive or gondola ride, hike to Moss Glen Falls, and lunch at The Whip Bar & Grill in the village.

Insider Local Tips

• Peak fall foliage is usually early to mid-October, but late September offers color with fewer visitors.
• Avoid Mountain Road traffic 4-6 PM on winter weekends; enjoy après-ski then leave later.
• Book peak ski weekends and foliage stays 6-12 months in advance; other times 4-6 months ahead works.
• For breakfast, try Stowe Bee Bakery & Cafe; Bingham Falls offers a scenic swimming hole hike.

Best Time to Visit Stowe

Fall and Winter draw the most visitors for foliage and skiing, respectively.

Burlington, VT

Burlington combines progressive urban charm with stunning lake and mountain views. This highly walkable city is perfect for couples, friends, and outdoors lovers wanting a food-focused, relaxing, and adventurous weekend. Its pedestrian-only downtown, craft beer culture, and access to Lake Champlain’s waterfront walkways enrich any visit.

Best Hotels to Stay in Burlington

• Hotel Vermont: Boutique hotel celebrating local craft with Vermont furnishings and the cozy Juniper restaurant onsite.
• Hilton Burlington Lake Champlain: Family-friendly hotel with stunning lake views and proximity to waterfront activities.
• Made INN Vermont: Unique boutique B&B with eclectic decor and a rooftop hot tub, ideal for couples seeking quirkiness.

Best Restaurants to Try in Burlington

• Hen of the Wood: High-end farm-to-table with daily-changing menus emphasizing local ingredients.
• American Flatbread: Casual organic, wood-fired pizzas paired with onsite brewed beer, capturing the local laid-back vibe.
• The Farmhouse Tap & Grill: Gastropub with one of Vermont’s best tap lists and a popular summer beer garden atmosphere.

Best Things to Do in Burlington

• Church Street Marketplace: Pedestrian thoroughfare with shops, cafes, and street performances.
• Burlington Greenway/Waterfront Bike Path: Eight-mile lakeside path perfect for biking with scenic views.
• Explore South End Arts District: Galleries, artist studios, and breweries offer a cultural offbeat experience.

2-Day Itinerary in Burlington

• Day 1: Check in and roam Church Street Marketplace. Dinner at The Farmhouse Tap & Grill beer garden.
• Day 2: Bike the waterfront Greenway, lunch and brews at Foam Brewers, and splurge dinner at Hen of the Wood.

Insider Local Tips

• Arrive early at the Burlington Farmers Market (Saturdays May-Oct) to avoid crowds and get the best picks.
• Venture south on Shelburne Road for family-friendly attractions like Shelburne Farms and the Vermont Teddy Bear Company.
• Book well ahead around University of Vermont events and peak fall foliage.
• For breakfast, skip lines by visiting The Friendly Toast; for sunset, enjoy a creemee on the waterfront.

Best Time to Visit Burlington

Summer and Fall when the outdoor scene and local events peak.

Frequently Asked Questions About Weekend Getaways in New England

What is the best time of year for a New England weekend trip? The best time depends on your goals: Summer is ideal for beaches and coastal towns, Fall offers world-famous foliage, especially in Vermont and New Hampshire, Winter suits ski trips, and Spring brings fewer crowds and lower prices.

Do I need to rent a car for a weekend getaway in New England? A car is highly recommended to explore most destinations and surrounding areas. However, in compact, walkable cities like Portland (ME), Portsmouth (NH), or Burlington (VT), you can manage without a car using ride-sharing services for airport transfers.

Which New England destinations are most romantic for a couples' trip? For luxury coastal charm, Newport (RI) and Kennebunkport (ME) shine. For cozy culture and great food, The Berkshires (MA) and Portsmouth (NH) are excellent. Portland (ME) offers vibrant food-focused city weekends.

How far in advance should I book accommodations, especially for fall foliage season? For peak fall foliage (late September to mid-October) and summer weekends, book 4-6 months in advance or earlier for popular hotels. Other times usually require 1-2 months advance bookings.

What's a realistic budget for a 3-day weekend in a popular New England town? Mid-range trips (e.g., Portland, Burlington) typically cost $250-$400 per person per day, including lodging, food, and activities. Luxury stays (e.g., Newport, Berkshires) can exceed $500-$700 per person daily.

Are there any walkable towns where I can park my car and not use it all weekend? Yes. Portland (ME), Portsmouth (NH), Burlington (VT), and Provincetown (MA) have highly walkable downtown areas with shops, restaurants, and hotels concentrated nearby.

Where are the distances and drive times calculated from? All distances and drive times are approximate from a central New England point in Worcester, Massachusetts. Actual times vary by your starting location, traffic, and time of day.

With this guide, choosing your next weekend getaway in New England is clear and manageable: from historic seaports to mountain retreats, each destination offers its own flavor of New England’s charm and hospitality, perfectly suited for your getaway weekend New England style.