Main Street News

With the holidays rapidly approaching, there are so many parades, markets, and other events coming up across the region. Though this is not a comprehensive guide, I’ve rounded up as many parades, markets, light shows, and other holiday events happening in the surrounding areas.

Basilica Farm & Flea Holiday Market 

Friday, November 28, Saturday, November 29, and Sunday, November 30 from 10am-5pm
Basilica Hudson, 110 South Front Street, Hudson, NY
basilicahudson.org/programs/farmandflea 

Basilica Hudson is hosting its holiday market on the weekend following Thanksgiving. Visit the market for all of your seasonal, local shopping needs, and make sure you come hungry, as Germantown’s Sweet Freedom Farm will be serving up sorghum syrup & waffles, and Staatsburg’s Breezy Hill Orchard will be toasting up woodfired pizza. Basilica Hudson is proud to present over 120 local businesses and vendors who are meaningful and essential contributors to the social and environmental health of the region. A full list of vendors is available on the Basilica Hudson site. 

Holiday Market at the Cannonball Factory

November 28-30, December 5-7, December 12-14, and December 19-21 from 11am-5pm
Cannonball Factory, 359 Columbia Street, Hudson, NY
cannonballfactory.com 

The most highly-attended holiday market in the Hudson Valley is back for a second season! The market will feature over 75 new vendors attending every weekend, including artisan foods, craft wines and spirits, vintage fashion and collectibles, natural beauty and skincare, and much more. 

Millerton’s Festival of Lights 

Friday, November 28
Village of Millerton, NY 

Millerton’s annual Festival of Lights returns on Friday, November 28. The festival runs throughout the day with family activities including a free movie screening at the Moviehouse at 10am, treats at Veteran’s Park from 11:30am-2:30pm, cookie decorating at the North East Community Center, a woodworking expo at the Irondale Schoolhouse, caroling along Main Street, and of course, the parade of lights at 5pm, hosted by the Millerton Fire Company. 

Festival of Trees at the Oliver Wolcott Library 

Saturday, November 29 from 5-8:30pm
The Oliver Wolcott Library, 160 South Street, Litchfield, CT
www.owlibrary.org/festival-of-trees.aspx 

The Festival of Trees event, a magical evening of festive celebration in support of the library, will feature a full open bar, lavish hors d’oeuvres, wreaths, trees, and so much more. All proceeds directly benefit library services, materials, and programs.

Sip, Sparkle & Stroll 

Saturday, November 29 from 4-8pm
Town of Kent, CT
kentct.com 

Get ready to Sip, Sparkle & Stroll your way through the charming town of Kent, CT! Returning this holiday season (previously known as the Champagne Stroll), this beloved community event invites guests to enjoy an evening of festive cheer, twinkling lights, and delightful sips as Kent’s shops, galleries, and restaurants open their doors for a night of celebration. Stroll along Kent’s Main Street and discover a variety of sparkling beverages, holiday treats, and unique shopping experiences — all while enjoying the warm and welcoming spirit that makes Kent so special. Whether you’re sipping with friends, supporting local businesses, or simply soaking in the holiday magic, this is a night not to be missed. 15% of ticket sales benefit the Kent Lions Club. 

Pine Plains Decorating Day and Parade of Lights 

Saturday, November 29 at 5pm
Town of Pine Plains, NY
For more information, visit the event’s Facebook.

Join the Town of Pine Plains in celebrating its 40th annual parade of lights on Saturday, November 29 at 5pm! Pick up tree decorations at the Bank of Millbrook in the center of town and help decorate a tree from 3-5pm. The parade will kick off at 5pm, travel through town from the high school parking lot, turn right at the stop light, and continue to the firehouse. 

Marton & Davis Holiday Social 

Sunday, November 30 from 11am-5pm
33 Main Street, Chatham, NY
martonanddavis.com 

Join Marton & Davis for a festive day at the shop, including custom calligraphed gift tags by Melissa Gamwell, holiday greenery by Damsel Garden, based in Stuyvesant, and the founders of Tu Et Al with the full alchemical skincare, soaps, and their brand new candle. 

The Millbrook Fire Department’s Annual Parade of Lights & Tree Lighting 

Friday, December 5 from 3-6pm
Village of Millbrook, NY 

The Millbrook Fire Department and Angels of Light will host the annual tree lighting on Friday, December 5 at 5:30pm. Prior to the tree lighting, Santa and Mrs. Claus will be available for photos at the Angels of Light office on Front Street from 3-5pm. Following the tree lighting, the parade of lights will kick off. Other festivities include caroling, warming fire cauldrons (donated by Orvis), a food drive to support the local food pantry, and a special appearance of Santa and Mrs. Claus, arriving by Millbrook Fire Engine! 

Holiday Market at Noble Horizons 

Friday, December 5, and Saturday, December 6 from 10am-4pm
Noble Horizons, 17 Cobble Road, Salisbury, CT
noblehorizons.org/events/holiday-market-2 

Join the folks over at Noble Horizons for a festive holiday market full of fun. Browse holiday gifts, enjoy free hot cider and donuts (while supplies last!), and stay for lunch with homemade soups, sandwiches, and sweets available for purchase. Storytime with Mrs. Claus will take place on Saturday, December 6 only. Proceeds directly benefit Noble Horizons residents.

Ancram Winterfest 

Saturday, December 6 from 1-5pm
Ancram Town Hall, 1416 County Route 7, Ancram, NY

Celebrate the holiday season at Ancram Winterfest! This free event hosts a variety of festivities that are fun for all ages, from cookie decorating, face painting, and a holiday sing-a-long to Santa’s visit at 4:30pm with a special gift for each child. Browse a local maker’s market, enter in the raffle, and sample seasonal treats and beverages, including a complimentary happy hour hosted by Fulton & Forbes. 

Winter Walk in Hudson 

Saturday, December 6 from 5-8pm
Warren Street, Hudson, NY
winterwalk2025.org 

Celebrating its 29th year, Hudson’s Winter Walk will usher in the holiday season with a street festival bursting with joy and wintery magic. This year’s celebration will feature bands, circus performers, dancers, choruses, costumed characters, fireworks, street food vendors, petting zoos, holiday lights and decorations, and much more.

Red Hook Parade of Lights 

Saturday, December 13 at 6pm
Village of Red Hook, NY 

Red Hook’s 5th annual parade of lights returns on Saturday, December 13. Lineup for the parade will begin at 4pm at the Red Hook Firehouse with a 6pm start time. There will be food trucks, amazing, creative floats, and a special appearance by Santa and Mrs. Claus! 

Wonderland of Lights at the Dutchess County Fairgrounds 

November 28-30, December 4-7, December 11-14, and December 18-28 from 5-9pm
6635 Spring Brook Ave, Rhinebeck, NY
thewonderlandoflights.com/dutchess-county-fairgrounds 

Celebrate the holidays at The Wonderland of Lights at the fairgrounds in Rhinebeck, NY! Featuring hundreds of dazzling displays to delight the entire family, the Wonderland of Lights is not to be missed. $30 per vehicle for up to eight passengers either online or at the gate. 

Winter Lights at Naumkeag 

November 28-January 3, Wednesdays through Sundays from 4:30-9pm
Naumkeag, 5 Prospect Hill Road, Stockbridge, MA
thetrustees.org/program/winterlights-massachusetts 

Winter Lights at Naumkeag are back for another wonderfully festive season. Head over to Stockbridge to enjoy the magical outdoor experience as Naumkeag’s grounds sparkle with thousands of shimmering and artfully-designed holiday lights. Bring the whole family for a fun outdoor experience. Ticket pricing and other information is available on the Naumkeag website.