Main Street News

With the holidays rapidly approaching, there are a variety of events and parades coming up all across the region. While this is by no means a complete guide, we’ve rounded up as many fairs, parades, and events that we could find for the surrounding area.

New York 

Winter Walk in Hudson
Saturday, December 2 from 5-8 p.m.

Hudson’s favorite winter street festival returns for its 27th year bigger and brighter than ever – rain or shine! Take an evening stroll down the mile-long length of historic Warren Street and enjoy performances, art installations, family-friendly attractions, local food and drinks, holiday shopping, fireworks and festive cheer. To learn more, visit their website here. 

Red Hook Parade of Lights
Saturday, December 9 at 6 p.m. 

The route will leave the fire house, enter into the Red Hook Estates, exit back out onto Route 9, drive through the village, turn on Park Ave, then turn on Linden Ave, before driving through the front half of Linden Acres and finally ending in College Park. 

Sinterklaas Festival Day in Rhinebeck
Saturday, December 2 from 10 a.m. to 8 p.m.

Sinterklaas is a day-long, colorful celebration that features children’s workshops, dance, theater and music all over the village of Rhinebeck. The spectacular Children’s Starlight Parade at 6:00 pm, featuring two-story tall, animated puppets carried by hundreds of volunteers, closes the day at twilight. A non-denominational event, Sinterklaas joins residents and visitors alike, people of all ages and backgrounds, in a memorable celebration of children, art, and the light of the winter season. To learn more about Sinterklaas and the day’s lineup of events, visit their website here. 

Wonderland of Lights at the Dutchess County Fairgrounds
November 22 through December 30 from 5-9 p.m. 

Join us for an unforgettable journey through a mesmerizing parade of twinkling lights, magical displays, and holiday cheer. From tunnel displays to towering structures and whimsical designs, The Wonderland of Lights will create a memorable experience for the entire family. $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. 

Pine Plains Decorating Day & Parade of Lights
Saturday, November 25 at 5 p.m. 

Decorating day will take place prior to the event from 3-5 p.m. 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. 

Millerton Festival of Lights Weekend
Friday, November 24 and Saturday, November 25 

Millerton Festival of Lights Weekend kicks off on Friday with an ice carving demonstration at Veterans Park, a free screening of The Grinch at the Moviehouse, cookie decorating, free hayrides, and a performance by the Salisbury Brass Band before the Festival of Lights Parade and Tree Lighting at 5 p.m. On Saturday, there will be a “Thankful for Reading” Event at the NorthEast Millerton Library at 12 pm. To learn more, visit Millerton’s website here. 

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 by November 30. On December 9, Santa will pay a visit to those who have submitted letters.

Millbrook Parade of Lights
Friday, December 1st at 6 p.m. 

The Millbrook Parade of Lights will take place on Friday, December 1. Line-up begins at 4:30 p.m. on Franklin Avenue next to MOST, and the parade officially steps off at 6 p.m. If you would like to volunteer to decorate, contact the Millbrook Business Association at mbapresident@millbrooknewyork.com and if you’d like to volunteer for the Parade of Lights, contact Cecilia Collopy at ceciliacollopy@gmail.com.  

Pleasant Valley Recreation Festival of Lights Parade
Saturday, December 2 at 6:45 p.m. 

Float line-up starts at 5:45 p.m. with large floats lining up on North Ave in front of the Village Park Apartments, small floats lining up on Ravine Road, and walkers lining up at the Bower Park entrance. 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 Sandy Coe at (845) 635-1111 ext. 203, email at scoe@pleasantvalley-ny.gov, or visit their website here. 

Amenia Celebration of Lights Parade
Sunday, December 3rd at 5 p.m. 

Activities including a visit with Santa, holiday arts and crafts, and a musical performance from the Webutuck Wildcats will take place from 3 p.m. to 5 p.m., with the tree lighting taking place at 4:45 p.m. 

Connecticut 

North Canaan Parade of Lights
Sunday, November 26 at 6 p.m. 

The parade lines up at the Stop & Shop at 5:30 p.m. and officially kicks off at 6 p.m. Following the parade, kids can visit with Santa under the pavilion at Lawrence Field. Holiday music will be performed by the Hot Cocoa Band, cookies and hot cocoa will be donated by the North Canaan Recreation Commission and Mountainside. To learn more, visit their Facebook page here. 

Festival of Trees at Noble Horizons
November 18 – December 2 

The Festival of Trees is free to attend and hours on Saturday through Wednesday are 12 p.m. to 4 p.m., and hours on Thursdays and Fridays: 12 p.m. to 6 p.m. 

Noble Horizons’ Gala Party will take place on Saturday, December 2 from 5 p.m. to 7:30 p.m. Tickets are $45. Pre-order by calling (860) 435-9851. Walk-ins are welcome. To learn more, visit their website here. 

Festival of Trees at The Oliver Wolcott Library
Saturday, November 25 at 5 p.m. 

It’s the most wonderful time of year for the folks over at The Oliver Wolcott Library! Tickets are on sale for their Festival of Trees event on November 25. The event will have a full open bar, hors d’oeuvres, wreaths and trees, and so much more. All proceeds directly benefit library services, materials, and programs. To learn how to purchase tickets, visit their website here. 

Annual Holiday Craft Fair
Saturday, December 2 at 12 p.m. 

The 3rd annual Holiday Craft Fair in Downtown Torrington takes place on December 2. Shop from 30+ local vendors featuring a variety of hand-crafted and local creations such as candles, jewelry, crochet and knit items, headbands, wreaths, pottery, and much more. Also enjoy a free showing of Elf in the Oneglia Auditorium at the Warner Theatre at 1 p.m. To learn more, visit their website here. 

Massachusetts 

Stockbridge: Main Street at Christmas
Friday, December 1 through Sunday, December 3 

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. Live performances, historic property tours, holiday markets, winter lights, unique shops, restaurants, and Santa show off the New England town. Capping off the weekend on Sunday, the town reenacts the spirit of Norman Rockwell’s famous holiday scene Stockbridge Main Street at Christmas, complete with vintage automobiles parked in the spots occupied in the painting. The day’s activities are sure to delight the child in everyone! To learn more, visit their website here. 

Holiday Shop, Sip & Stroll
Saturday, December 9 from 3-8 p.m. 

The Southern Berkshire Chamber presents the 2023 Holiday Shop, Sip & Stroll on Saturday, December 9 with family-friendly activities throughout downtown Great Barrington. To learn more about the event, visit their website here.