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8 Winter Weekend Getaways in New England

Boston is beautiful year-round, but sometimes it's to escape outside of the city in the winter months

Winter activities in New England are not limited to skiing and snowboarding—there are plenty of outdoor activities to do that would not necessarily draw your attention once summer begins. 

Here are 8 destinations to spend a long weekend trip in other parts of New England:

West Hartford, Connecticut

  • Estimated Travel Time from Boston: < 2-hour drive 
  • What to See & Do:
    • Visit Connecticut's Children Museum 
    • Take a short drive to see classic American author Mark Twain's house
  • Dinner Date: avert Brasserie 
  • Where to Stay: Delamar West Hartford 

Stowe, Vermont

  • Estimated Travel Time from Boston: > 3.5-hour drive; > 6.5-hour bus ride 
  • What to See & Do:
    • Take in the wintry weather at Stowe Mountain Resort's scenic trails
    • Hit the slopes at Mount Mansfield for downhill skiing
    • Tour Ben & Jerry's Ice Cream factory
  • Dinner Date: Cork Wine Bar & Market
  • Where to Stay: Field Guide 

Portsmouth, New Hampshire

  • Estimated Travel Time from Boston: < 1.5-hour drive; 2-hour bus ride
  • What to See & Do:
    • Explore the restaurants and shops in Market Square 
    • Visit the Strawberry Banke Museum to see what colonial life in Portsmouth, NH was like
    • Spend the afternoon at Book & Bar, an old-fashioned bookshop that serves light fare and has live entertainment 
  • Dinner Date: Surf Portsmouth
  • Where to Stay: The Hotel Portsmouth

Newport, Rhode Island

  • Estimated Travel Time from Boston: < 1.5-hour drive
  • What to See & Do:
    • Visit the historic Gilded Age mansions on Bellevue Avenue
    • Explore The Cliff Walk from Easton's Beach to Salve Regina University's campus
    • Wine tasting at Newport Vineyards in nearby Middletown, RI
    • Enjoy local nightlife by bar hopping along Broadway, Newport's main scene for locals
  • Brunch: The Clarke Cooke House
  • Dinner Date: Stoneacre Brasserie, Castle Hill Inn
  • Where to Stay: Gilded

Kennebunkport, Maine

  • Estimated Travel Time from Boston: < 2-hour drive
  • What to See & Do:
    • Ski, snowshoe or walk in the National Estuarine Research Reserve of Wells Reserve
    • Shop around Dock Square and Kennebunk's Lower Village
    • Relax during a spa treatment at Whit Barn Inn & Hotel by Grace Hotels
  • Dinner Date: Bandaloop, 2 Dock Square, Kennebunkport
  • Where to Stay: Kennebunkport Inn

Providence, Rhode Island

  • Estimated Travel Time from Boston: < 1-hour drive; < 1-hour via Northeast Regional Commuter Rail
  • What to See & Do:
    • Visit Rhode Island School of Design (RISD) Museum
    • Go ice skating in the downtown Bank of America ice rink
    • Take a self-guided walking tour along Benefit Street to see historic colonial homes
  • Brunch: The Duck and Bunny 
  • Where to Stay: The Dean Hotel

Rockport, Massachusetts

  • Estimated Travel Time from Boston:  < 1-hour drive;1.5-hour T ride via Newburyport/Rockport Line 
  • What to See & Do:
    • Walk around downtown Rockport along Bearskin Neck neighborhood for unique New England shopping
    • Visit the Twin Lighthouses, among the oldest lighthouses in the United States
    • Grab your camera and explore Halibut Point State Park to see beautiful views of Cape Ann
  • Dinner Date: Feather & Wedge
  • Where to Stay: Emerson Inn

New Haven, Connecticut

  • Estimated Travel Time from Boston: < 3-hour drive; 2-hour Acela train ride
  • What to See & Do:
    • Visit Yale Peabody Museum of Natural Museum
    • See the largest collection of PEZ products at the PEZ Visitor Center 
    • Taste classic New Haven pizza at Frank Pepe's Pizzeria
  • Dinner Date: Olea (Spanish/Mediterranean) 
  • Where to Stay: The Study at Yale


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