10 New England Towns to Visit During the Holidays

Before I jump into this post, I'd recommend bookmarking these places for travel in future years. As the situation with the pandemic and restrictions are constantly changing, I know personally day trips I was hoping to make this season have been cancelled as it just seems too risky and irresponsible. Of course, I am not a scientist or medical professional, so please refer to the professionals for guidelines. 

In more normal years, loads of New England towns transform into the most magical places during the holidays. It is quintessential New England at its finest. From storefronts decked out in holiday style, dazzling lights strung about, and glistening snow blanketing the ground, villages look like they're straight out of a Hallmark movie. 

Over the years I've compiled a small list of lovely places I always make a point to visit and I thought I'd share it with you, so you can share in the magic!

Portsmouth, NH

This port city is simply beautiful during the holiday season. As with many towns, there is an impressive tree standing tall in the center of town. The surrounding streets lined with shops offer a variety of products and decorations to gawk at. A bit away from downtown are narrow roads with charming colonial homes nestled in and naturally dressed to the nines!

Kennebunkport, ME

*Heart eyes* KPT is such a special little seaside village. Yet another quaint town with oodles of mom and pop shops! Kennebunkport has some of the most beautiful houses, impressive decor, and fun activities to enjoy, like Prelude. There's just something about seeing the massive KPT letters across from the bridge reflecting on the water that makes my heart swoon.

For more about Kennebunkport, check out this post here and this outfit one here.

Portland, ME

Portland, ME is arguably one of my favorite cities of all time. From the local watering holes to the best donuts around, modern decor shops, and the cutest stationary store; this hub has a lot to offer year-round.

Woodstock, VT

Woodstock is a not so hidden gem anymore, and it makes sense why. It is beyond charming. The stunning Woodstock Inn sits in the center of town with a quiet grandeur. One of the most picturesque covered bridges in New England is across the way, as well. And don't forget about Sleepy Hollow Farms!

Burlington, VT

On the shore of Lake Champlain resides a bustling city called Burlington. With a New England and French Canadian influence, there is so much to love and enjoy in this city. The food and drink scene is great, along with the various museums around. Church Street is wonderful to stroll up and down during the holidays, as well.

Newport, RI 

Newport takes the top spot for my favorite town to visit during the holidays specifically. Since high school I've gone most years around Christmas and the excitement never dulls. Each time I visit I discover more in the area and it is simply wonderful. It has a special place in my heart as a nerd for historic homes and member of the Preservation Society. Plus, I almost went to school in town at Salve!

Best known for the Newport Mansions, aka the "summer cottages" of American Royalty, the Preservation Society exquisitely maintains and decorates them for the holidays. The poinsettia trees in the expansive ballrooms are striking. Bellevue Avenue is just something else. Certainly that part of Newport is fabulous, but truly all of the downtown is charming and so fun to explore.

Springfield, MA

Western MA is great. It is so under appreciated, despite there being so much to do. Over the last few years I've gotten to know Western MA much better, as my boyfriend is from the area. It's been a blast exploring! Springfield specifically has so many different museums to check out, including one for Dr. Seuss, as he is from the city (you can even drive along the real Mulberry Street). They also have a brand new MGM casino. A bit more understated, but so magical is a yearly event called Bright Nights set up in Forrest Park. The city creates some truly incredible light displays. I think it'd make anyone giddy driving through while listening to Christmas tunes.

Deerfield/South Deerfield, MA

Heading towards the Berkshires is Deerfield and South Deerfield, MA. Deerfield has a beautiful historic district. Would recommend having a drive or walk through there. Right in South Deerfield is the flagship Yankee Candle Store... and it's insane. For details on that experience, definitely check out this post here.

Boston, MA

Beantown is the best place to be during the holidays! Well one of the best if you're into big cities. Though with the various neighborhoods, it feels like such a small homey city. Of course there is plenty of shopping for gift gathering with Newbury Street, Faneuil Hall, and beyond. My favorite spot to be is Beacon Hill and the North End.

Mystic, CT

Admittedly, I've yet to go to Mystic, CT, and likely won't this winter, but I have seen loads of photos of this cute coastal city. Everyone raves about it! They have such an adorable lighthouse, too. 

Have you been to any of these towns?