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13 Hallmark-Worthy New England Towns To Visit For A Winter Break Road Trip From Montreal

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13 Hallmark-Worthy New England Towns To Visit For A Winter Break Road Trip From Montreal
  • Here are 13 towns perfect for a New England road trip from Montreal.
  • We selected each of these places specifically for their winter sights, activities, and difference from Montreal.
  • Along with each item on the list, you'll find the drive time from Montreal and a link to a municipal website for more information.

Winter is here and we're already disillusioned. Once the excitement of the holidays fades away, Montrealers are left facing a four-month block of wintry weather with little to motivate them. So begins the sluggish cycle of work, sleep, and Netflix until the late spring thaw unlocks our collective, suppressed spirit. Amid the winter gloom, adventures out of the city can be the best thing to both shake up that dull routine and maintain mental health. So we've put together this list of easy New England road trips to make the most of the cold season.

Each town and city on this list was selected specifically for its winter activities and sights. They're also all within six driving hours of the Montreal and offer views and experiences that you'd be hard-pressed to find in Quebec.

Not on this list are any of New England's biggest cities — Boston, Cambridge, Worcester, Burlington. These are all quiet, small settlements with a way of life a world removed from that of congested Montreal.

From sleepy coastal communities to valley villages with thriving arts and craft scenes, here are the New England towns to check out this winter!



Drive time from Montreal: 5 hours

Concord is a go-to holiday shopping destination for many a Bostonian looking to stroll among its quaint colonial storefronts. The large common (a central park in a New England town) also provides plenty of opportunity for Christmas photos.

Stop by the famous Concord Colonial Inn for brunch with characters re-enacting life in Revolutionary Massachusetts!



Drive time from Montreal: 5 hours

Newburyport is a coastal village famous for its 18th-century mansions, brick façades, and dense centre filled with small retailers and artisan shops, many of which are made to attract Instagram hungry tourists.



Drive time from Montreal: 4 hours 30 minutes

Home to Smith College and near both Mount Holyoke College and the flagship campus of the University of Massachusetts, Northampton is known for its activist population, progressive politics, and LGBTQ culture.

The town centre has an abundance of cafés, but venture out to some of the art galleries to truly discover what makes Northampton great!



Drive time from Montreal: 5 hours 20 minutes

Locals claim that the red storehouse on Bear Neck is the most painted building in the United States. Though difficult to prove, the legend speaks to Rockport's picturesque quality.

Walk down the Neck browsing galleries and fudge shops before venturing back into the town centre and strolling between its many charming abodes.

The village at the tip of Massachusetts' Cape Ann has even served as the backdrop for many a Hollywood movie (including The Proposal starring Canada's own Ryan Reynolds).



Drive time from Montreal: 4 hours 15 minutes

Tucked among the Berkshire Mountains, this town in western Massachusetts is quintessential Americana. It's even home to the museum of Norman Rockwell, whose paintings of mid-20th-century American life defined the era and inspired the contemporary cultural perception of the 50s.

Also in Stockbridge is the famous Red Lion Inn and a municipal calendar packed with events dedicated to arts and crafts.


New Hampshire


Drive time from Montreal: 4 hours 30 minutes

The quiet town of Exeter outside the larger city of Portsmouth (listed below) is perhaps better for a quick visit than an extended stay.

The old properties outlined with white picket fences festooned in garland for the holidays are Hallmark-worthy.

On Front Street, stand atop the bandstand and enjoy views of the eclectic commercial centre.



Drive time from Montreal: 3 hours 15 minutes

Home to Ivy League Dartmouth College, Hanover has just about everything you'd expect: large campus green spaces, student bars and cafés, and collegiate, 18th-century American architecture.



Drive time from Montreal: 4 hours

Oh, look! Another cute bandstand that will make you feel like Lorelei Gilmore wandering the streets of Stars Hollow, coffee in hand!

The centrepiece of the town holiday decorations is the giant Christmas tree, which, if the location tag on Instagram is any indication, is a popular spot for photos.



Drive time from Montreal: 4 hours

Meredith sits at the northern tip of the sprawling Lake Winnipesaukee and is a popular stopping point for skiers headed to the White Mountains.

In his town, you'll find a number of cute hotels and stores, the best of which can be found in the converted old mill in the town centre.



Drive time from Montreal: 5 hours

The colonial capital of New Hampshire is still a working seaport and is actually home to an exciting culinary scene, the highlight of which, of course, is the seafood.

Market Square almost feels like a Disney theme park with its brick buildings and narrow streets.




Drive time from Montreal: 2 hours 20 minutes

The capital of Vermont fits snugly in a valley in the Green Mountains along the Winooski River and, despite its status as the least populous state capital in the United States, has plenty to do and see.

In the winter, you can go ice skating on the State House grounds or shop along the — well, stately State Street, where you can also catch a movie at a retro theatre.

The best part of Montpelier is undoubtedly its characters. Think stereotypical, lovable Vermonter: plaid, boots, colourful t-shirt. It's a fun community to visit.



Drive time from Montreal: 2 hours 30 minutes

This college town has nature walks that take you through snow-covered woods and past waterfalls. Spend the night in one of the many inns and bed & breakfasts after hitting one the nearby slopes.



Drive time from Montreal: 3 hours 20 minutes

The municipal website does a pretty good job of selling this town: "steeped in New England character and the picturesque beauty of the Green Mountains, Woodstock, Vermont is a colorful, four-season destination that harnesses the spirit of independence and craftsmanship."

Book a room at the Woodstock Inn and be sure to visit the many galleries and theatres. Don't leave without getting a photo of a covered bridge!


Where are you off to next?

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