There’s nothing so quintessentially lovely as wandering down a charming main street during the holidays. Shop windows glow, Christmas lights twinkle, and the smell of warm spices and cider fill the air. Check out some of the most picturesque and spirited main streets in Massachusetts this holiday season.
- Nantucket
Flickr/MOTT Under a light layer of snow, Nantucket’s main street looks like a holiday card come to life. Already one of the quaintest towns in the state, this island community pulls out all the stops to make sure walking downtown feels like a special holiday treat. Stop by on Christmas Stroll Weekend from December 2-4 for a particularly festive experience.
- Newburyport
Flickr/MOTT Newburyport is a dreamy seaside town that lights up at Christmastime. Filled with little shops and cozy restaurants that seem to glow with holiday cheer, your best bet for the ultimate charming stroll is to wander around Market Square and by the docks. Stop by A Partridge in a Bear Tree for adorable holiday decorations and gifts.
- Concord
Flickr/MOTT Concord is a quiet town that is loaded with holiday charm. Their annual Christmas stroll and parade winds through downtown on December 2, and brings plenty of light and laughter to the town’s main street. Check out The Toy Shop of Concord and pick up a thoughtful, old-fashioned toy for a special child in your life.
- Faneuil Hall Marketplace, Boston
Flickr/MOTT Though it’s not quite a typical main street, the cobbled streets that run through Quincy Market have a charming air that makes the area feel especially magical during the holidays. There are nightly light shows every 30 minutes, and plenty of opportunities for holiday shopping.
- Rockport
Flickr/Tania & Artur Rockport is definitely better known for its summertime charm, but the town’s main street is just as attractive in the snow. Little shops and side streets are bedecked in garlands and lights, and the smell of the sea adds nautical charm to the holiday scene. On Christmas morning, head to the harbor to watch Santa arrive on a lobster boat.
- Taunton
Wikimedia Commons Taunton’s main street and town square transform into a winter wonderland during the holidays. The town has been putting on a fine holiday show since 1914, and its nickname is “The Christmas City.” Check out their annual holiday parade on December 4, and admire the town’s lights through the New Year.
- Somerville
Flickr/emdurso Somerville is centered around town squares rather than one particular main street, but those squares are the perfect places to go and enjoy the town’s holiday glamour. Somerville has one of the largest numbers of Christmas light displays around Boston, so it’s a great destination for an urban holiday stroll.
- Deerfield
Flickr/MOTT The beauty of the Pioneer Valley truly shines in Deerfield during the snowy season. A journey along this historic town’s main street will yield gorgeous views of colonial homes, old-fashioned decorations and cozy, snowy inns. Stop by the Deerfield Inn at 81 Main Street for delicious, farm to fork holiday treats.
- Stockbridge
Flickr/Mark Goebel Norman Rockwell’s favorite haunt makes for a magical Christmas destination. Strolling down Main Street in Stockbridge feels like taking a journey back in time. The look of Stockbridge’s main street at Christmas has changed little since Rockwell painted the quaint scene. It’s definitely worth wandering by the Red Lion Inn and enjoying a hot cocoa on the porch. Be sure to stop by the “Stockbridge Main Street at Christmas” event December 2 - 4.
- Framingham
Flickr/Barbara L. Slavin Though it might not be on the main drag, Framingham’s restored 1870s Main Street bridge is the perfect place to take in a spectacular snowy view. The bridge
- Provincetown
Flickr/Robin Woltman Provincetown is another one of those summer destinations that’s actually a wonderful place to visit around the holidays. Check out the classic lobster trap “Christmas tree,” and browse the shops and art galleries that line the downtown streets.
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Flickr/MOTT
Under a light layer of snow, Nantucket’s main street looks like a holiday card come to life. Already one of the quaintest towns in the state, this island community pulls out all the stops to make sure walking downtown feels like a special holiday treat. Stop by on Christmas Stroll Weekend from December 2-4 for a particularly festive experience.
Newburyport is a dreamy seaside town that lights up at Christmastime. Filled with little shops and cozy restaurants that seem to glow with holiday cheer, your best bet for the ultimate charming stroll is to wander around Market Square and by the docks. Stop by A Partridge in a Bear Tree for adorable holiday decorations and gifts.
Concord is a quiet town that is loaded with holiday charm. Their annual Christmas stroll and parade winds through downtown on December 2, and brings plenty of light and laughter to the town’s main street. Check out The Toy Shop of Concord and pick up a thoughtful, old-fashioned toy for a special child in your life.
Though it’s not quite a typical main street, the cobbled streets that run through Quincy Market have a charming air that makes the area feel especially magical during the holidays. There are nightly light shows every 30 minutes, and plenty of opportunities for holiday shopping.
Flickr/Tania & Artur
Rockport is definitely better known for its summertime charm, but the town’s main street is just as attractive in the snow. Little shops and side streets are bedecked in garlands and lights, and the smell of the sea adds nautical charm to the holiday scene. On Christmas morning, head to the harbor to watch Santa arrive on a lobster boat.
Wikimedia Commons
Taunton’s main street and town square transform into a winter wonderland during the holidays. The town has been putting on a fine holiday show since 1914, and its nickname is “The Christmas City.” Check out their annual holiday parade on December 4, and admire the town’s lights through the New Year.
Flickr/emdurso
Somerville is centered around town squares rather than one particular main street, but those squares are the perfect places to go and enjoy the town’s holiday glamour. Somerville has one of the largest numbers of Christmas light displays around Boston, so it’s a great destination for an urban holiday stroll.
The beauty of the Pioneer Valley truly shines in Deerfield during the snowy season. A journey along this historic town’s main street will yield gorgeous views of colonial homes, old-fashioned decorations and cozy, snowy inns. Stop by the Deerfield Inn at 81 Main Street for delicious, farm to fork holiday treats.
Flickr/Mark Goebel
Norman Rockwell’s favorite haunt makes for a magical Christmas destination. Strolling down Main Street in Stockbridge feels like taking a journey back in time. The look of Stockbridge’s main street at Christmas has changed little since Rockwell painted the quaint scene. It’s definitely worth wandering by the Red Lion Inn and enjoying a hot cocoa on the porch. Be sure to stop by the “Stockbridge Main Street at Christmas” event December 2 - 4.
Flickr/Barbara L. Slavin
Though it might not be on the main drag, Framingham’s restored 1870s Main Street bridge is the perfect place to take in a spectacular snowy view. The bridge
Flickr/Robin Woltman
Provincetown is another one of those summer destinations that’s actually a wonderful place to visit around the holidays. Check out the classic lobster trap “Christmas tree,” and browse the shops and art galleries that line the downtown streets.
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