The holiday season on Gloucester Main Street features twinkling lights, cute shops, and the delicious scents wafting from our renowned restaurants creating an irresistible atmosphere of festive wonder.
Immerse yourself in a journey where the allure of yesteryear seamlessly mingles with the vibrancy of today. Gloucester Village, a cherished hub that has stood the test of time for over three centuries, invites you to rediscover its enduring charm – a place where the holiday spirit thrives year-round.
Gloucester’s Main Street kicks off the holidays with the enchanting First Friday when art takes center stage. Stroll with friends and family and experience a world of joyful holiday experiences, courtesy of our unique shops, galleries, restaurants, and museums.

Gloucester’s Main Street kicks off the holidays with the enchanting First Friday when art takes center stage. Stroll with friends and family and experience a world of joyful holiday experiences, courtesy of our unique shops, galleries, restaurants, and museums.
Saturday: Unleash the Magic of the Christmas and Holiday Parade as creative floats, lively bands, and local organizations take center stage in the nostalgic Christmas and Holiday Parade, commencing at 3:00 pm. Stay with us on Main Street as the sun sets to witness the inspiring annual Community Tree-Lighting Ceremony and sing along carols at 5:00 pm in the Historic Court Circle.

Sunday: A Festive Grand Finale closes out the weekend with the enchanting Holiday Open House from 1:00 pm to 5:00 pm. Immerse yourself in the holiday spirit as you explore Main Street’s charming shops and eateries. Savor delectable holiday treats, engage in festive activities, join the harmonious caroling with the Liberty Dolls, and capture cherished moments with Santa Claus. Roasting s’mores and seasonal shopping deals await, along with enchanting sleigh rides to make your visit truly magical.
Experience the timeless charm of Gloucester Village and be a part of an unforgettable holiday celebration.
Mark your calendar with these key dates:
DECEMBER 1:
First Friday, an immersion into our community’s arts and culture through galleries, eateries, and small businesses on Gloucester Main Street.
DECEMBER 2:
Christmas & Holiday Parade/ Community Tree Lighting, featuring over 40 floats, bands, and community groups that will ignite the holiday spirit. The Parade commences at 3:00 pm, and the Community Christmas Tree lights up at 5:00 pm in the Historic Court Circle.
DECEMBER 3:
Holiday Open House, a delightful kickoff to the holiday season, where you can explore Main Street shops and restaurants from 1:00 pm to 5:00 pm. Enjoy holiday treats, festive activities, caroling, and create lasting memories with Santa Claus.