Festive Places To Visit In New England For The Holidays

By Kelley Boymer
15 Nov 2022
Festive Places To Visit In New England For The Holidays

New England is a quintessential place to visit during the holiday season straight out of a Norman Rockwell painting. The weather is cool and crisp, snow flurries are falling and holiday cheer is in the air. The ambiance in New England is a magical, winter wonderland that brings you all the warm, nostalgic holiday feels. The charming towns of New England look like miniature-scale holiday villages that have come to life. With so many things to see and do in New England during this time, it can be hard to choose which ones to visit. With everything from Christmas tree lightings on Village Greens and visits with Santa to annual Christmas celebrations and Christmas decorations adorning streets, shops, restaurants and quaint B&B’s– the holidays in New England are so unique and special.

If you’re looking for some fun travel to do in New England this holiday season, here is a round-up of the best festive places to visit in New England that will surely get you in the holiday spirit.

Festive Places To Visit In New England For The Holidays

Woodstock, Vermont

Things To Do During The Holidays In Woodstock, VT

We may be biased and honestly Woodstock, Vermont is our favorite year round– but especially during the holidays. Our little town lights up like a classic Hallmark movie. Frequently voted as one of the best Christmas towns in the U.S. with trees twinkling with white Christmas lights in the village, snow blanketing the ground and true magic everywhere you look. This winter wonderland of holiday events begins with Thanksgiving, when our community comes together for the annual Zack’s Place Turkey Trot, a fundraiser for our local community enrichment center. Thanksgiving Weekend at Billings Farm showcases 19th century crafts, traditions and foods for the whole family to enjoy!

Wassail Weekend truly rings in the start of the holiday season with the annual Wassail Parade. This parade features over 50 horses, period dress and holiday costumes. Over the course of the weekend you can enjoy holiday house tours, caroling, and horse carriage rides. Be sure to take a picture under the Middle Covered Bridge, (located just across from the Village Green) in the distance you will see the star lit from the top of Mt. Tom. While you’re in town, don’t miss Christmas at Billings Farm, Wassail Weekend at Billings Farm and BarnArts Holiday Cabaret: Let it Snow.

Where To Stay During The Holidays In Woodstock, VT

Take your pick from Woodstock’s charming B&Bs and inns to host your stay. Some of our favorites include: The Woodstock Inn, The Jackson House Inn, The Vesper, The Blue Horse Inn and The Woodstocker B&B. Check out The Woodstock Guide for over curated 100 recommendations designed to use on mobile or desktop.

Newport, Rhode Island

Things To Do During The Holidays in Newport, RI

It’s no secret that Newport is one of our favorite Christmas towns. The Newport coast is a beautifully scenic place to enjoy your holiday celebrations this season. The historic charm of Newport brings so much to their holiday celebrations. Walk down cobblestone streets sparkling with twinkling lights and shops and restaurants dressed up in holiday cheer. Newport has an array of events to enjoy throughout the holiday season including– Holidays at the Newport Mansions, Newport Illuminated Boat Parade, Bowen’s Wharf Christmas Tree Lighting, and Newport Nutcracker at Rosecliff. Check out The Newport Guide for 100s of recommendations on what to see, do, eat and where to stay.

Where To Stay During The Holidays In Newport, RI

Newport hotels dress up in style for the holidays and there is nothing better to make you feel festive for the season. Try The Vanderbilt, The Chanler, or Castle Hill Inn.

Portsmouth, New Hampshire

Things To Do During The Holidays in Portsmouth, NH

The gorgeous seacoast is the perfect place to enjoy the holiday season in Portsmouth, New Hampshire. Portsmouth’s vintage Christmas feels like warmth, light and everything we know and love about a classic New England Christmas. This city lights up for the holidays with amazing shows at the Music Hall Historic Theater, the Annual Gingerbread House Contest & Exhibition, outdoor skating at Strawbery Banke Museum and the Illuminated Holiday Parade and Tree Lighting. We love everything about Portsmouth during the holidays!

Where To Stay During The Holidays In Portsmouth, RI

The Hotel Portsmouth is the perfect spot to host your stay while in the city. Or try Wentworth by the Sea, A Marriott Hotel & Spa or the Stage Neck Inn— an oceanfront boutique resort in York Harbor (20 minutes outside of Portsmouth).

Taunton, Massachusetts

Things To Do During The Holidays In Taunton, MA

For those looking for the festiveness of the city with a small town feel, Taunton, MA is the perfect getaway this holiday season. Their notable Lights on Festival and Lighting of the Taunton Green includes magical light displays, activities for the whole family to enjoy and live performances. If you can’t make it for the lighting you can enjoy the twinkling display all season long and enjoy the museum, library, town green and state park while you are in town.

Where To Stay During The Holidays In Taunton, MA

Stay at the Colonel Blackinton Inn just 20 minutes out of town for that intimate New England B&B feel.

Boston, Massachusetts

Things To Do During The Holidays In Boston, MA

Boston is such a fun city during the holidays. It provides enough of the festive city holiday cheer, while also feeling manageable and not too overwhelming. There is ample opportunity to enjoy holiday activities like ice skating at the Boston Common Frog Pond, holiday theater and shows, Holiday Lights Trail, Stone Zoo’s ZooLights, Holiday Pops, shopping and dining amongst twinkling lights and cheerful city streets and so much more!

Where To Stay During The Holidays In Boston, MA

Try the Newbury Boston or Whitney Hotel for a warm boutique, intimate hotel experience in a big city.

Jackson, New Hampshire

Things To Do During The Holidays In Jackson, NH

Spend your Christmas season in the White Mountains in Jackson, NH. This beautiful little Christmas town features their very own Christmas Farm Inn & Spa, head to Nestlenook Farm for sleigh rides, ice skating and snowshoeing, visit Jackson’s famous covered bridge and join in the festivities at the Annual Inn to Inn Cookie Tour and Traditionally Yours Celebration. Christmas time in Jackson is charming and will fill you with warmth and light this season!

Where To Stay During The Holidays In Jackson, New Hampshire

Stay in a quaint B&B while enjoying your holiday in Jackson– try The Inn at Thorn Hill or the Christmas Farm Inn & Spa.

More Of Our Favorite New England Holiday Getaways

Freeport, Maine

Sparkle Celebration Parade of Lights

Newburyport, Massachusetts

Santa Parade and Tree Lighting

Stockbridge, Massachusetts

Main Street at Christmas

Kennebunkport, Maine

Christmas Prelude

Mystic, Connecticut

Festival of Lights

Edgartown, Massachusetts

Christmas in Edgartown

Where do you enjoy visiting during the holiday season in New England? What are your favorite holiday events to enjoy in New England? Let us know in the comments below.

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3 Comments

  1. Caro wrote:

    Is the Berkshires reference a typo for Taunton? Taunton is closer to RI/the cape.

    11.17.22 | Reply
    • LG wrote:

      I was just going to say the same! Taunton is not in the Berkshire’s. For those not familiar with the area this could create a lot of confusion.

      11.19.22 | Reply
    • Yes, sorry this was a typo. Thank you for letting us know! It has been fixed.

      11.22.22 | Reply