Main Street News

With the holidays rapidly approaching, there are so many events and parades coming up all across the region. While this is by no means a complete guide, we’ve rounded up as many light shows, markets, parades, and other holiday events that we could find in the surrounding areas.

New York 

Hudson Pop-Up Holiday Market at the Cannonball Factory
Saturdays & Sundays from November 23 to December 22 

The first annual Pop-Up Holiday Market at the Cannonball Factory is coming to Hudson, NY, this season! Featuring over 20+ market vendors, delicious food trucks, warm drinks, and bonfire hangouts for family and friends at the Cannonball Factory on Columbia Street. The market will run from 10:30am to 5pm on November 23-24, December 7-8, December 14-15, and December 21-22. 

Millbrook Parade of Lights
Friday, December 6 at 6pm 

The Millbrook Parade of Lights will take place on Friday, December 6. Line-up begins at 4:30pm on Franklin Avenue at the entrance to Front Street near the firehouse, and the parade officially steps off at 6pm. The Village of Millbrook is looking for businesses, organizations, teams, or individuals to participate in the Parade of Lights with a float or decorated vehicle to celebrate the holiday season. If you would like to volunteer to participate, contact the Millbrook Fire Department at secretary@millbrookfirerescue.org or visit their website here. 

Millerton Festival of Lights
Friday, November 29 

The Millerton Festival of Lights kicks off on Friday, November 29th. Lineup starts at 4pm at Arnoff Moving & Storage. Additionally, any Millerton or Northeast resident who would like a visit from Santa can write their letter to Santa and put it in the mailbox at the firehouse. On Saturday, December 14, Santa will pay a visit to those who have submitted letters. To learn more, visit the Millerton Fire Company’s Facebook page here. 

Pine Plains Decorating Day & Parade of Lights
Saturday, November 30 at 5pm 

Decorating day will take place prior to the event from 3 to 5pm. Town Christmas trees lining the sidewalks are decorated, visits with Santa take place, and cookies and cocoa are available. The parade starts at the high school, turns right at the light in town, and ends at the firehouse.

Pleasant Valley Recreation Festival of Lights Parade
Saturday, December 7 at 6:45pm 

Float line-up begins at 5:45pm with large floats lining up on North Avenue in front of Village Park Apartments and walkers lining up at the Bower Park Exit (8 Ravine Rd). Visit Santa after the parade at the Town Hall upper parking lot! There will also be a Season of Giving Food Drive – donate at drop boxes located in the Town Hall lobby and the Pleasant Valley Fire Department. For parade information, contact Recreation Director Nikki Santos at (845) 635-1111 ext. 203, email nsantos@pleasantvalley-ny.gov, or visit their website here. 

Red Hook Parade of Lights
Saturday, December 14 at 6pm 

The parade kicks off at 6pm from the Red Hook Firehouse, and then travels to the outside of the Red Hook Estates, Route 9 through the village, up Park Avenue to Linden Acres, and finishes off in College Park. Food trucks will be serving food in the Village Hall municipal parking lot and there will be donation boxes for unwrapped toys for Toys for Tots outside of Little Pickles Toy Store. If you’re interested in having your business or family join the parade, call or text Kyle Streib at (845) 249-1548, or visit the parade’s Facebook page here. 

Winter Walk in Hudson
Saturday, December 7 from 5-8pm. 

Presented by The Foundry at Hudson, Hudson’s favorite winter street festival returns to Warren Street for its 28th year. Bring the whole family for an evening filled with live music, joyous performances, holiday shopping, competing window displays, delicious treats, and a fireworks show presented by Hudson Hall. This year, they’ve also got some surprises in store, so don’t miss out! To learn more, visit their website here. 

Wintermarkt at the Vanderpoel House
Saturday, December 7 from 11am to 5pm

Wintermarkt at the Vanderpoel House, located at 16 Broad Street in Kinderhook, is a holiday market featuring twelve local makers. The 1820 house will be filled with artisanal, handmade, and antique gifts, and also coincides with the Columbia County Historical Society’s Gallery of Wreaths, a silent wreath auction. The Vanderpoel House will be outfitted with over 40 wreaths, donated from the Wintermarkt vendors and the local community. 

Wonderland of Lights at the Dutchess County Fairgrounds
November 28 through December 29 from 5-9pm 

Celebrate the holidays at The Wonderland of Lights at the fairgrounds in Rhinebeck! Featuring hundreds of dazzling displays to delight the entire family, the Wonderland of Lights is not to be missed! Open from November 28-December 1, December 5-8, and nightly from December 12-29. $30 per vehicle for up to eight passengers either online or at the gate. For more ticketing options and more information, visit their website here.  

Connecticut 

Festival of Trees at The Oliver Wolcott Library
Saturday, November 30 from 5-8:30pm 

It’s the most wonderful time of year for the folks over at The Oliver Wolcott Library! The Festival of Trees event will have a full open bar, lavish hors d’oeuvres, wreaths, trees, and so much more. All proceeds directly benefit library services, materials, and programs. To learn more or purchase tickets, visit their website here. 

Holiday Market at Noble Horizons
December 6 + 7 from 10am to 4pm 

The Noble Horizons Holiday Market is a festive, community event offering a wide variety of locally crafted gifts, artisanal goods, and holiday decorations. Held in the community room at Noble Horizons in Salisbury, CT, the market features unique handmade items, jewelry, baked goods, and more! Whether you’re looking for handcrafted ornaments or gourmet treats, the market is a festive and welcoming experience for all ages. For more information, visit the Noble Horizons website here. 

Litchfield Holiday Stroll
Sunday, December 8 at 3pm 

Ring in the holiday season from 3-5pm at the Litchfield Green. Events include a choral performance by the Plumb Hill Middle School chorus, ornament making at the Litchfield Historical Society, cookie decorating with the Girl Scouts at the Congregational Church, and hot chocolate with the Boy Scouts at the center of town. The tree lighting will take place at 5pm. To learn more, visit the Litchfield event calendar here. 

North Canaan Parade of Lights + Winter Fest
Sunday, December 1 from 3-8pm 

Hosted at North Canaan Elementary School by the North Canaan Events Committee, Winter Fest will include vendors, food, and visits with Santa! You can also watch the parade of lights from the elementary school. If you’re a vendor interested in participating, you can reach out to the events committee at northcanaaneventscommittee@gmail.com to claim a spot. To learn more about the parade and the festival, visit their website here. 

Massachusetts 

Holiday Shop, Sip & Stroll
Saturday, December 14 at 2pm

Presented by the Southern Berkshire Chamber of Commerce, the annual Holiday Shop, Sip & Stroll returns to downtown Great Barrington with free fun for the whole family! Kick off events will happen from 2-4pm, and then activities, crafts, and games will take place throughout downtown from 4-7pm, wrapping up with fireworks and a concert at Saint James Place. To learn more, visit the Southern Berkshire Chamber of Commerce’s website here. 

Nightwood: A Fantastical Journey Through Sound and Light
Weekends and select weekday evenings from November 22 to January 4 from 5-8pm

Drawing inspiration from the natural world of The Mount, Nightwood is a unique sound and light immersion that takes visitors on a one-mile illuminated path through the woods and gardens of Edith Wharton’s Gilded Age Estate in Lenox. Children 12 and under are free, and tickets are available for purchase at the Edith Wharton website here. 

The Pevzner Family Annual Christmas Display
November 28 through December 31 from 5-9pm 

The Pevzner Family Annual Christmas Display is on Brush Hill Road in Great Barrington. Pevzner has been putting lights up for about 20 years, but they increased their display to include over 40,000 lights. The light display is on from 5-9pm from Thanksgiving to New Year’s Eve. 

Stockbridge: Main Street at Christmas
Friday, December 6 through Sunday, December 8 

The town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge: Main Street at Christmas. Sponsored by the Stockbridge Chamber of Commerce, the holiday celebration offers a full range of holiday activities for the entire family to enjoy, including live performances, historic property tours, holiday markets, winter lights, and visits with Santa. Capping off the weekend, on Sunday, the town reenacts the spirit of Norman Rockewell’s famous holiday scene of Main Street at Christmas. To learn more, visit their website here. 

Winter Lights at Naumkeag
Wednesdays through Sundays from November 29 through January 4 

Winter Lights at Naumkeag in Stockbridge are back! Join them for a magical outdoor experience at Naumkeag, as it sparkles with thousands of shimmering and artfully designed holiday lights. Bring the whole family for a fun, safe outdoor experience. Advanced purchase of timed tickets is required and tickets will not be sold on site. For more information about tickets and parking, visit their website here.