Christmas in CT: Festive Main Streets for a Holiday Stroll

Christmas in Connecticut is a magical time! There are holiday events throughout the state, light displays, theater performances, and so much more. Add holiday parties, shopping, and decorating, and you could easily spend 24/7 on Christmas, no doubt leaving you overstimulated, exhausted, and maybe even a bit bah humbug.

If I don’t give myself some downtime from all of the festivities it is a recipe for disaster. One of my favorite ways to unwind, indulge in some self-care, and still enjoy the holiday spirit is to take a walk where many of the homes are decorated for Christmas. It gives me some much-needed exercise and fresh air, and allows me to really notice my surroundings. Alone or in pairs, here are some of my favorite main streets to enjoy a holiday stroll in Connecticut.

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Main Street in Suffield, CT

Suffield is a Hartford County town that borders Massachusetts (in fact it was once part of Massachusetts due to a surveying error), about 16 miles north of Hartford. It is a quiet place, with lots of open space and farmland. Although the town was known for paper manufacturing in its early days, like many Connecticut River Valley towns its longest standing industry was tobacco.

The Main Street of Suffield definitely captures the feeling of Christmas in Connecticut. The entire street is part of the Suffield Historic District, with grand homes of almost every architectural style built from the early 18th to mid-20th centuries. Though the length of the district is over two miles, I would suggest parking at the Suffield Town Green and walking a loop down a portion of South Main, then double back to walk a portion of North Main. The homes have a nice setback, so walk down one side of the street first, cross, and then walk back on the other side.

Though the majority of the district is residential, there are a few churches, some newer businesses, as well as Suffield Academy, a private, co-ed secondary school that attracts students from all over the country and world.

Bundle up and take a nice walk down Main Street in Suffield – it does not disappoint! If you are looking to do something before or after, the stunning Phelps-Hathaway House has some weekend holiday activities, as does the King House (both are normally closed in the winter). Warm up and grab a bite at Three Figs, just off the Green, as well!

North and South Streets in Litchfield, CT

We go from the quiet, lesser known town of Suffield, CT to perhaps one of the most well-known, picture perfect towns in Connecticut: Litchfield. Litchfield developed into a prosperous commercial and legal center early in its history, and by 1810 the town had earned a national reputation as an educated and cultured community. After a temporary decline, the town was booming again when it became a seasonal resort attracting wealthy summer residents.

Before heading to Litchfield, print yourself a copy of this fabulous map from the Litchfield Historical Society which will tell you where to go and give you some background as well. Find a parking spot somewhere around the Litchfield Town Green which has a number of monuments and a strategically placed Congregational church which was quoted by The New York Times as being a “New England icon”.

I recommend strolling a portion of South Street first, turning back towards the Green and then stopping for nourishment at The Village Restaurant, a longtime Litchfield institution. Maybe pop into South Street Antiques, or have a coffee and treat at the new bakery/cafe Dottie’s Provisions. It is absolutely darling! If you’re ambitious, you can then walk (or drive!) North Street.

Main Street and the Broad Street Green in Wethersfield, CT

Are you sensing a theme here? Many of the most beautiful areas to experience Christmas in Connecticut are towns that focus around a town green that the rest of the community has developed around. Wethersfield is no different, and the largest historic district in the state of Connecticut centers around the Broad Street Green and its neighboring Main Street. It’s hard to imagine that in the 1920s the State wanted to run a new highway right through the Green (the Silas Deane Highway). What a loss that would have been!

Similar to Litchfield, a nice walking guide is available to help you plan your holiday stroll which is three miles long at its full length but can be shortened to your taste. Upon arriving in Old Wethersfield, park in the general vicinity of Comstock Ferre. Walking North on Main Street will lead you to Wethersfield Cove, and heading South will take you to Garden Street. Take a left on Garden Street and in a few minutes you will find yourself on the Broad Street Green.

A highlight of the Green is the Silas W. Robbins House Bed & Breakfast, an impressive and immaculately maintained Second Empire home. It was recently featured in the Hallmark Christmas film “Christmas on Honeysuckle Lane” as were many other Old Wethersfield locales. That should tell you just how special this area is, and there is no better way to see it than by foot.

If you are interested in more than just a stroll, plan a visit to the Webb-Deane-Stevens Museum which has multiple properties in the historic district. During the holidays, three of their historic homes are decorated in the fashion of three different centuries to show how the holidays have evolved over time. Have a meal by the fire at Lucky Lou’s in the 1787 Deming-Standish House, or enjoy a slice at the Greek pizzeria Village Pizza which has been a local favorite for over 30 years.

Old Main Street in South Windsor, CT

While I highly recommend all of the places mentioned thus far, and I have enjoyed them on frequent occasion, Old Main Street in South Windsor, CT is near and dear to my heart. Christmas in Connecticut is not complete for me until I have strolled down Old Main Street during the day, or driven down the street at night to see the holiday lights. I grew up in South Windsor, and my parents still live in town as do some of my oldest friends.

I would suggest parking at the Wood Memorial Library or somewhere along the street. Unlike the other areas mentioned, Old Main Street in South Windsor is primarily a residential street with no significant commercial enterprise. As such, it has minimal traffic. Pick a direction to walk and turn around when it suits you to head the other direction.

The architecture on Old Main Street spans the centuries with almost every historic style represented from Federal to Greek Revival to Gothic Revival. Mixed throughout are a number of farmhouses, barns, and other structures which add to the overall charm of the historic district, as noted in the recent book presented by the Connecticut Trust for Historic Preservation entitled Connecticut Architecture: Stories of 100 Places (a must buy for anyone who loves architecture, history, Connecticut, or any combination of the above!)

If you time it right, either before or after your holiday stroll stop by the Gingerbread House Festival at the Wood Memorial Library & Museum. Every year it has a different theme, and the gingerbread artists are so creative! And be sure that you walk to or drive by the East Windsor Hill Post Office at the end of Old Main Street, considered by some to be the oldest continuously operating post office in the country.

I hope these suggestions inspire you to take a drive to an area that is new to you for a fresh way to experience Christmas in Connecticut. It will be good for your soul, burn a few calories, and you might even learn something new. Do you have a favorite area to walk during the holidays? I know there are other beautiful places out there to enjoy so please leave your suggestions in the comments!

You can also shop some of my favorite Etsy finds for Connecticut lovers here, including these Connecticut hand crafted ornaments:

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