The Most Festive Main Streets of Connecticut During Christmas

December 24th, 2018
Location  •   Litchfield, Connecticut

Preppy New England Couple The Coastal Confidence Aubrey Yandow

Christmas in New England The Coastal Confidence Aubrey Yandow
The Most Festive Main Streets of Connecticut During Christmas The Coastal Confidence Aubrey Yandow

It’s really starting to feel like Christmas, and while the last couple of weeks have been a whirlwind, this past weekend was the perfect opportunity for our crew to wind down with work and enjoy the best of Connecticut in Christmas. During this time of year, I love exploring the surrounding towns and their Main Street’s, specifically to enjoy the decorations and shop at the locally owned stores. In fact, you can always find the best antique shops and boutiques on, or just off, the Main Streets of New England.

With that being said, I wanted to share some of the most festive main streets of Connecticut during Christmas time. I hope everyone has a chance to explore New England during the most wonderful time of the year. So whether you’re heading out to a holiday party or here visiting family for the week; add these towns to your list!

Preppy Holiday Style The Coastal Confidence Aubrey Yandow
Preppy Couple Holiday Style The Coastal Confidence Aubrey Yandow
Preppy Couple Holiday Style The Coastal Confidence Aubrey Yandow
Festive Holiday Towns To Visit In Connecticut The Coastal Confidence

The Most Festive Main Streets of Connecticut During Christmas:


+ Main Street, Litchfield: I think Litchfield wins most festive Main Street in all of Connecticut. From evergreen wrapped light posts to wreaths adorning every store window, you’ll feel as if you’ve been transported into a Christmas movie almost instantly. In fact, Matt and I snapped these pictures before heading to our Christmas Eve party in Main Street, Litchfield this year!

+ Main Street, Essex: If you like historic homes, you’ll love seeing them all decked out during the most wonderful time of the year. Make sure to stop into Essex Coffee & Tea Company, to grab a large hot cocoa before walking the streets and taking in the festive home decor with your loved ones.

+ Pratt Street, Hartford: If you’re a 90’s child, like myself, who grew up in Connecticut you might remember going to see the G. Fox Christmas display, come the most magical time of the year. It was certainly a sight to be seen and has been sincerely missed since its closure. However, this year Pratt Street is taking on the tradition, as the animatronic dolls once used in the G. Fox Christmas display will be on exhibit in the old Lux Bond & Green on Pratt Street! Make sure to stop by and check it out on your way to Hartford’s Winterfest.

+ Main Street, Mystic: Nobody seems to embrace Connecticut’s colonial history as much as Mystic during the Christmas season. Between holiday lantern tours and restaurants decked out in classic Christmas evergreen, you’ll be sure to be in the holiday spirit in no time.

+ Post Road, Westport: If you’re looking to get some holiday shopping, head to Westport to take in their stunning holiday window contest. From local restaurants, to name brand stores, this Main Street will have you checking off your gift list in a jiffy while getting you in the holiday mood! I recommend heading here in the late afternoon, or evening so you can see the store windows all lit up!

Silver Holiday Party Skirt The Coastal Confidence Aubrey Yandow
Best towns for Christmas shopping in Connecticut The Coastal Confidence Aubrey Yandow
M.Gemi Corsa Boots The Coastal Confidence Aubrey Yandow
Preppy Holiday Style The Coastal Confidence Aubrey Yandow
J.McLaughlin Holiday Style The Coastal Confidence Aubrey Yandow

I want to take some time to wish you all a safe and Merry Christmas. Our crew is taking the next week off to relax, reorganize and look back on 2018. With that being said, we wanted to say thank you for reading, and I can’t wait to share more of New England with you all in 2019! Have a wonderful Christmas!

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