Boston’s dynamic city life offers endless excitement, but sometimes, a rejuvenating escape is in order—whether for relaxation, adventure, romance, or family fun. With its prime location, Boston is the ideal launchpad for a variety of unforgettable weekend getaways. This 2025 guide presents the region’s top destinations, tailored recommendations for every type of traveler, practical itineraries, and expert insights to help you plan your next memorable journey.
Quick Picks – Best Getaways by Season & Traveler Type
A successful weekend escape hinges on timing and fit. Use this table to quickly match your interests and the season to the perfect getaway:
| Spring | Summer | Fall | Winter | |
| Couples | Newport, RI | Martha’s Vineyard | Berkshires | Woodstock, VT |
| Families | Cape Cod | Portsmouth, NH | Salem, MA | North Conway, NH |
| Solo | Providence, RI | Portland, ME | Northampton, MA | Stowe, VT |
| Pet Owners | Rockport, MA | Ogunquit, ME | Mystic, CT | Newburyport, MA |
This matrix streamlines decision-making, drawing on seasonal highlights and traveler needs. For example, couples seeking a romantic fall retreat will find the Berkshires’ foliage and cozy inns compelling, while families might prefer the festive atmosphere and museums of Salem in October.
Interactive Map of Weekend Getaways from Boston
Explore all featured destinations using our interactive map below. Each pin reveals travel time, top attractions, and links to detailed guides. Most getaways are within a 2–3 hour drive, making them perfect for a short escape.
Top 18 Weekend Getaways from Boston
Boston’s proximity to New England’s treasures means there’s a getaway for every mood. Here, we present a curated selection—each offering distinct experiences, practical tips, and original insights.
1. Cape Cod, Massachusetts
Why Visit?
Cape Cod draws visitors with its windswept beaches, historic lighthouses, and charming villages. Beyond the popular shores of Hyannis and Provincetown, discover the Cape Cod Rail Trail for cycling, and lesser-known gems like Wellfleet’s art galleries.
Best Things to Do
- Bike the 25-mile Rail Trail
- Explore Provincetown’s vibrant arts scene
- Whale watching from Barnstable Harbor
- Visit Heritage Museums & Gardens
Where to Stay
Opt for the Chatham Bars Inn for classic luxury, or the Salt House Inn in Provincetown for a boutique touch. Budget travelers should consider seaside motels in Dennisport; most are open year-round.
Where to Eat & Drink
Try Mac’s Shack in Wellfleet for fresh seafood or the Lobster Pot in Provincetown. For a local experience, sample fried clams from a roadside shack.
Sample 2-Day Itinerary
Day 1: Beach time at Coast Guard Beach, lunch in Chatham, biking the Rail Trail.
Day 2: Morning in Provincetown, whale watching, dinner at a waterfront restaurant.
Getting There & Transportation Tips
Cape Cod is a 1.5-hour drive from Boston. During peak summer, consider the CapeFLYER train or Peter Pan Bus to avoid traffic.
Budget Breakdown
- Lodging: $120–$400/night
- Dining: $15–$50/meal
- Activities: Many beaches are free; whale watching tours ~$60
Accessibility & Pet-Friendly Notes
Several beaches (e.g., Mayflower Beach) are wheelchair accessible. Many accommodations and trails welcome dogs.
2. Newport, Rhode Island
Why Visit?
Steeped in Gilded Age opulence, Newport’s famed mansions, scenic Cliff Walk, and vibrant harbor make it a perennial favorite. Off-season, enjoy quieter streets and discounted tours.
Best Things to Do
- Tour The Breakers and Marble House
- Walk the 3.5-mile Cliff Walk
- Sailboat cruises in Narragansett Bay
- Visit the International Tennis Hall of Fame
Where to Stay
The Chanler at Cliff Walk offers a romantic, historic stay. Family-friendly options include Newport Marriott; budget travelers may prefer boutique B&Bs inland.
Where to Eat & Drink
Try The Mooring for local seafood or Brick Alley Pub for a casual bite. Newport’s coffee shops are perfect for harbor views.
Sample 2-Day Itinerary
Day 1: Morning mansion tour, afternoon at Easton’s Beach, sunset cruise.
Day 2: Cliff Walk, brunch downtown, exploration of Thames Street shops.
Getting There & Transportation Tips
About 90 minutes from Boston by car; Amtrak to Providence plus RIPTA bus is a car-free alternative.
Budget Breakdown
- Lodging: $150–$500/night
- Dining: $20–$60/meal
- Attractions: Mansion tours ~$25–$30
Accessibility & Pet-Friendly Notes
Cliff Walk is partially accessible; many hotels and parks are pet-friendly.
3. The Berkshires, Massachusetts
Why Visit?
A haven for nature lovers and culture seekers. Famed for fall foliage, hiking, and a thriving arts scene, the Berkshires offer both outdoor adventure and world-class performing arts.
Best Things to Do
- Hike Mount Greylock (Massachusetts’ highest peak)
- Visit the Norman Rockwell Museum
- Explore Tanglewood’s summer concerts
- Tour Hancock Shaker Village
Where to Stay
The Red Lion Inn in Stockbridge provides historic charm; for unique stays, try glamping at Race Brook Lodge.
Where to Eat & Drink
Enjoy farm-to-table fare at Prairie Whale or stop at Tunnel City Coffee for local brews.
Sample 2-Day Itinerary
Day 1: Hike or drive Mount Greylock, afternoon at the Clark Art Institute.
Day 2: Visit Lenox’s bookstores, afternoon at Hancock Shaker Village.
Getting There & Transportation Tips
A 2.5-hour drive west. Limited bus service from Boston is available via Peter Pan Lines.
Budget Breakdown
- Lodging: $100–$350/night
- Dining: $15–$45/meal
- Attractions: Museums ~$20
Accessibility & Pet-Friendly Notes
Many museums are accessible; several trails and lodges are pet-friendly.
4. Portsmouth, New Hampshire
Why Visit?
A lively seaport town blending history, arts, and waterfront charm. Portsmouth is ideal for families and culture enthusiasts with walkable streets, historic houses, and kid-friendly museums.
Best Things to Do
- Tour Strawbery Banke Museum’s living history exhibits
- Stroll Market Square for boutique shopping
- Visit the Children’s Museum of New Hampshire
- Take a harbor cruise
Where to Stay
Try The Hotel Portsmouth for a boutique stay, or Residence Inn Downtown for family-friendly suites. Budget travelers can check inns along Route 1.
Where to Eat & Drink
Enjoy fresh oysters at Row 34, casual bites at Portsmouth Brewery, or ice cream at Annabelle’s.
Sample 2-Day Itinerary
- Day 1: Morning at Strawbery Banke, Market Square lunch, evening harbor cruise
- Day 2: Children’s Museum, brunch, and Prescott Park gardens
Getting There
Just an hour drive from Boston; C&J Bus Lines offers car-free options.
Budget Breakdown
Lodging: $120–$300/night
Dining: $15–$45/meal
Attractions: $15–$25
Accessibility & Pet-Friendly Notes
Downtown is mostly walkable and wheelchair accessible; many hotels allow pets.
5. Portland, Maine
Why Visit?
A foodie’s paradise with coastal charm. Portland is packed with breweries, lighthouses, and art. Great for solo travelers and couples.
Best Things to Do
- Tour Portland Head Light
- Brewery hop along the Maine Beer Trail
- Visit Portland Museum of Art
- Ferry to Peaks Island
Where to Stay
The Press Hotel offers chic luxury; budget-friendly options include local B&Bs or motels outside downtown.
Where to Eat & Drink
Try Eventide Oyster Co. for lobster rolls, Duckfat for fries, and Allagash Brewery for craft beer.
Sample 2-Day Itinerary
- Day 1: Art museum, brewery hopping, Old Port dining
- Day 2: Lighthouse visits, ferry to Peaks Island
Getting There
2-hour drive or Amtrak Downeaster train from Boston.
Budget Breakdown
Lodging: $130–$400/night
Dining: $20–$60/meal
Attractions: $10–$30
Accessibility & Pet-Friendly Notes
Old Port’s cobblestones are uneven; most breweries and parks are pet-friendly.
6. Salem, Massachusetts
Why Visit?
Known for its witch trial history, Salem is a must in October. But it’s equally rich in museums, art, and maritime history year-round.
Best Things to Do
- Visit the Salem Witch Museum
- Explore Peabody Essex Museum
- Tour The House of the Seven Gables
- Stroll Derby Wharf
Where to Stay
Hawthorne Hotel offers historic elegance; The Hotel Salem gives modern boutique vibes.
Where to Eat & Drink
Enjoy seafood at Turner’s, or cocktails at Ledger.
Sample 2-Day Itinerary
- Day 1: Witch trial museum, walking tour, waterfront dinner
- Day 2: Peabody Essex Museum, shopping, The House of the Seven Gables
Getting There
30 minutes by car or direct commuter rail from Boston.
Budget Breakdown
Lodging: $110–$300/night
Dining: $15–$45/meal
Attractions: $10–$25
Accessibility & Pet-Friendly Notes
Many museums are accessible; several hotels allow dogs.
7. Stowe, Vermont
Why Visit?
A winter wonderland for skiing and a charming summer/fall retreat with hiking and foliage.
Best Things to Do
- Ski or snowboard at Stowe Mountain Resort
- Drive through Smugglers’ Notch
- Visit Stowe Cider
- Hike Moss Glen Falls
Where to Stay
Topnotch Resort offers luxury, while inns like Green Mountain Inn are cozy and affordable.
Where to Eat & Drink
Try Hen of the Wood for fine dining or Piecasso for casual pizza.
Sample 2-Day Itinerary
- Day 1: Morning ski, après-ski cider tasting
- Day 2: Scenic drive and waterfall hike
Getting There
3.5-hour drive from Boston; bus service available.
Budget Breakdown
Lodging: $120–$500/night
Dining: $20–$60/meal
Lift tickets: ~$120/day
Accessibility & Pet-Friendly Notes
Resorts offer accessibility services; many trails and inns welcome dogs.
8. Rockport, Massachusetts
Why Visit?
A classic seaside escape with art galleries, coastal walks, and lobster shacks.
Best Things to Do
- Visit Bearskin Neck shops
- Explore Halibut Point State Park
- See Motif No. 1, Rockport’s famous fishing shack
- Relax on Front Beach
Where to Stay
Rockport Inn & Suites or seaside B&Bs like Addison Choate.
Where to Eat & Drink
Roy Moore Lobster Co. is iconic for lobster rolls.
Sample 2-Day Itinerary
- Day 1: Explore Bearskin Neck, seafood dinner
- Day 2: Halibut Point hike, beach day
Getting There
1-hour drive or MBTA commuter rail.
Budget Breakdown
Lodging: $120–$280/night
Dining: $15–$40/meal
Attractions: Mostly free
Accessibility & Pet-Friendly Notes
Downtown is walkable; many inns accept pets.
9. Ogunquit, Maine
Why Visit?
Known for sandy beaches and the scenic Marginal Way cliff walk.
Best Things to Do
- Walk Marginal Way
- Relax at Ogunquit Beach
- Visit Ogunquit Playhouse
- Explore Perkins Cove
Where to Stay
Anchorage by the Sea or cozy B&Bs like Meadowmere Resort.
Where to Eat & Drink
Barnacle Billy’s is perfect for seafood with a view.
Sample 2-Day Itinerary
- Day 1: Marginal Way walk, Perkins Cove dinner
- Day 2: Beach day, Playhouse show
Getting There
1.25-hour drive from Boston.
Budget Breakdown
Lodging: $120–$350/night
Dining: $20–$60/meal
Attractions: Mostly free
Accessibility & Pet-Friendly Notes
Marginal Way has accessible portions; dog-friendly beaches off-season.
10. Providence, Rhode Island
Why Visit?
A vibrant small city known for arts, history, and culinary excellence.
Best Things to Do
- RISD Museum
- Federal Hill dining
- WaterFire art installation (seasonal)
- Roger Williams Park
Where to Stay
Dean Hotel for trendy stays; chain hotels for budget.
Where to Eat & Drink
Al Forno for Italian, Seven Stars for coffee.
Sample 2-Day Itinerary
- Day 1: RISD Museum, WaterFire evening
- Day 2: Roger Williams Park, Federal Hill food tour
Getting There
1-hour drive or Amtrak from Boston.
Budget Breakdown
Lodging: $100–$250/night
Dining: $15–$50/meal
Attractions: Free–$20
Accessibility & Pet-Friendly Notes
City attractions are accessible; several dog-friendly hotels.
11. North Conway, New Hampshire
Why Visit?
A gateway to White Mountain adventures and outlet shopping.
Best Things to Do
- Conway Scenic Railroad
- Hike Diana’s Baths
- Shop Settlers Green Outlets
- Ski Cranmore Mountain
Where to Stay
Red Jacket Mountain Resort (family-friendly with water park).
Where to Eat & Drink
Delaney’s Hole in the Wall for comfort food.
Sample 2-Day Itinerary
- Day 1: Scenic railroad, outlet shopping
- Day 2: Hike, afternoon ski or drive the Kancamagus Highway
Getting There
3-hour drive from Boston.
Budget Breakdown
Lodging: $120–$350/night
Dining: $15–$45/meal
Attractions: Free–$30
Accessibility & Pet-Friendly Notes
Some trails accessible; many lodgings pet-friendly.
12. Northampton, Massachusetts
Why Visit?
An artsy, LGBTQ+ friendly college town with music, museums, and bookstores.
Best Things to Do
- Visit Smith College Museum of Art
- Browse independent bookstores
- Explore music venues and local art galleries
- Bike the Norwottuck Rail Trail
Where to Stay
Hotel Northampton or budget-friendly Airbnbs.
Where to Eat & Drink
Hungry Ghost Bread or Paul & Elizabeth’s.
Sample 2-Day Itinerary
- Day 1: Art museum, bookstore crawl
- Day 2: Rail Trail bike ride, local music show
Getting There
2-hour drive from Boston.
Budget Breakdown
Lodging: $90–$250/night
Dining: $10–$40/meal
Attractions: Free–$15
Accessibility & Pet-Friendly Notes
Downtown mostly accessible; dog-friendly B&Bs available.
13. Mystic, Connecticut
Why Visit?
Famous for its maritime history and aquarium.
Best Things to Do
- Mystic Seaport Museum
- Mystic Aquarium
- Downtown shops and Mystic Pizza
- Kayak tours
Where to Stay
Inn at Mystic or budget motels nearby.
Where to Eat & Drink
Mystic Pizza (made famous by the movie) and Oyster Club.
Sample 2-Day Itinerary
- Day 1: Seaport Museum, pizza dinner
- Day 2: Aquarium visit, kayaking
Getting There
2-hour drive from Boston; Amtrak accessible.
Budget Breakdown
Lodging: $110–$280/night
Dining: $15–$50/meal
Attractions: $20–$35
Accessibility & Pet-Friendly Notes
Aquarium and seaport are accessible; pet-friendly hotels available.
14. Newburyport, Massachusetts
Why Visit?
A charming coastal town with shops, dining, and nearby Plum Island.
Best Things to Do
- Plum Island beaches
- Explore Parker River Wildlife Refuge
- Stroll downtown shops
- Take a whale watch tour
Where to Stay
Essex Street Inn or Plum Island rentals.
Where to Eat & Drink
Brine for oysters, or Grog for pub fare.
Sample 2-Day Itinerary
- Day 1: Wildlife refuge, beach picnic
- Day 2: Downtown stroll, whale watch tour
Getting There
1-hour drive or commuter rail from Boston.
Budget Breakdown
Lodging: $100–$250/night
Dining: $15–$45/meal
Attractions: Free–$50
Accessibility & Pet-Friendly Notes
Plum Island has accessible boardwalks; many pet-friendly inns.
15. Woodstock, Vermont
Why Visit?
One of New England’s prettiest villages, great for couples.
Best Things to Do
- Explore Billings Farm & Museum
- Walk covered bridges
- Shop village boutiques
- Ski Killington nearby
Where to Stay
Woodstock Inn for upscale stays; Airbnbs for budget.
Where to Eat & Drink
Mon Vert Café for breakfast, Worthy Kitchen for craft beer.
Sample 2-Day Itinerary
- Day 1: Covered bridges, village stroll
- Day 2: Billings Farm, nearby skiing or hiking
Getting There
2.5-hour drive from Boston.
Budget Breakdown
Lodging: $120–$400/night
Dining: $15–$50/meal
Attractions: $10–$25
Accessibility & Pet-Friendly Notes
Town is walkable and accessible; several inns pet-friendly.
16. Lenox, Massachusetts
Why Visit?
Cultural hub of the Berkshires with Tanglewood concerts and historic mansions.
Best Things to Do
- Attend Tanglewood in summer
- Tour The Mount (Edith Wharton’s home)
- Visit Berkshire Botanical Garden
Where to Stay
Cranwell Spa or small B&Bs.
Where to Eat & Drink
Alta for Mediterranean fare.
Sample 2-Day Itinerary
- Day 1: Tanglewood, downtown stroll
- Day 2: The Mount, botanical garden visit
Getting There
2.5-hour drive from Boston.
Budget Breakdown
Lodging: $110–$350/night
Dining: $20–$60/meal
Attractions: $20–$40
Accessibility & Pet-Friendly Notes
Most cultural sites accessible; many inns pet-friendly.
17. Kittery, Maine
Why Visit?
Known for outlet shopping and coastal dining, just over the NH border.
Best Things to Do
- Shop Kittery Premium Outlets
- Visit Fort Foster
- Explore local breweries
Where to Stay
Budget hotels near outlets or seaside inns.
Where to Eat & Drink
Bob’s Clam Hut for fried seafood.
Sample 2-Day Itinerary
- Day 1: Outlet shopping
- Day 2: Fort Foster and coastal walk
Getting There
1-hour drive from Boston.
Budget Breakdown
Lodging: $90–$220/night
Dining: $10–$40/meal
Attractions: Mostly free
Accessibility & Pet-Friendly Notes
Outlets and parks are accessible; pet-friendly motels available.
18. Burlington, Vermont
Why Visit?
A lakeside city blending college-town energy, outdoor adventure, and craft beer.
Best Things to Do
- Stroll Church Street Marketplace
- Visit Lake Champlain waterfront
- Explore local breweries
- Bike the Burlington Bike Path
Where to Stay
Hotel Vermont or boutique Airbnbs.
Where to Eat & Drink
Hen of the Wood (fine dining), Foam Brewers (craft beer).
Sample 2-Day Itinerary
- Day 1: Marketplace shopping, brewery tour
- Day 2: Bike path ride, lakefront picnic
Getting There
3.5-hour drive from Boston; limited bus/train.
Budget Breakdown
Lodging: $130–$400/night
Dining: $20–$60/meal
Attractions: Free–$20
Accessibility & Pet-Friendly Notes
Bike path accessible; city offers pet-friendly hotels.
How to Choose the Perfect Weekend Getaway
Selecting the right destination means balancing interests, logistics, and timing. For beach getaways, Cape Cod and Ogunquit shine in summer, while the Berkshires and Stowe offer peak foliage in October. Families with young children might prioritize destinations with aquariums or science museums (Portsmouth, Mystic), while couples seeking seclusion may opt for the tranquil lakes of New Hampshire. Car-free travelers should consider Newport, Portland, or Providence, all accessible by train and bus.
Planning Your Trip – Pro Tips & Packing Essentials
- Best Times to Go:
Spring and fall offer mild weather and fewer crowds. Book well in advance for summer weekends. - What to Pack:
Layers are key for New England’s changeable weather. Don’t forget rain gear, comfortable shoes, travel chargers, and, for winter trips, snow boots. - Booking Advice:
Peak weekends (Memorial Day, Labor Day, fall foliage) fill up quickly. Check for off-season deals in November–April. - Local Etiquette & Safety:
Many small towns prize quiet evenings; respect local customs and parking rules. Always check for seasonal road closures.
FAQs
What are the closest weekend getaways to Boston?
Salem, Rockport, and Portsmouth are less than 90 minutes away, making them ideal for quick escapes.
Are there car-free travel options for weekend trips?
Yes. The CapeFLYER train, Amtrak, and regional buses offer routes to Cape Cod, Providence, Newport, and more.
What’s the best time of year for a getaway from Boston?
Late spring and early fall for mild weather and fewer crowds; summer for beaches; winter for ski towns.
Which destinations are pet-friendly?
Cape Cod, Rockport, and North Conway have numerous dog-friendly lodgings and trails.
How do I find budget-friendly accommodations?
Look for off-season rates, motels, and vacation rentals. Many museums offer free or discounted days.
Are these destinations family-friendly and accessible?
Most highlighted getaways offer accessible attractions and family-oriented activities. Always check individual sites for details.
Related Resources & Further Reading
- Best Day Trips from Boston
- Hidden Gems in New England
- Family-Friendly Attractions Near Boston
- Pet-Friendly Travel in New England
