Seasonal & Holidays
2025 Woodbury Holiday Guide: Lights, Festive Fun & Good Cheer
From small-town charm to seasonal celebrations, these hometown holiday highlights bring the spirit of the season to life.
The holiday season has arrived in Woodbury, bringing twinkling lights, cheerful events and plenty of ways to make memories close to home. From light displays to beloved local traditions, here are the hometown holiday highlights you won’t want to miss.
Please note: Dates and details are subject to change, so be sure to check with each organizer before you go — many events require tickets or reservations in advance.
An Old-Fashioned Wassail & Holiday Celebration
When: Friday, Dec. 5, 2025 | 5:30–8 PM
Where: Glebe House Museum & Gertrude Jekyll Garden, 49 Hollow Rd, Woodbury, CT
Find out what's happening in Woodbury-Middleburyfor free with the latest updates from Patch.
Sip traditional hot mulled cider, enjoy holiday music, and experience an old-fashioned Yuletide celebration inside one of Woodbury’s most historic homes. Guests are encouraged to don cozy festive attire for an evening of wassailing, seasonal treats and a warm, candlelit atmosphere. Tickets are required for this event.
More info: glebehousemuseum.org
Find out what's happening in Woodbury-Middleburyfor free with the latest updates from Patch.
Ceramic Holiday Tree & Ornament Paint and Sip
When: Friday, Dec 5, 2025 | 6–8 PM
Where: Tranquillity Vineyard & Winery, 1892 Middlebury Rd, Middlebury, CT
Enjoy a festive night of creativity as you sip wine and paint your own ceramic holiday tree and wood-slice ornament with guidance from Annie’s Art Party. Your ticket covers all supplies and step-by-step instructions, so you can relax and enjoy the process. This hands-on workshop offers a cozy, social atmosphere perfect for a seasonal night out, and you’ll head home with handmade décor to brighten your holiday season.
More info: tickettailor.com/events
Bethlehem Christmas Town Festival
When: Friday–Saturday, Dec. 5–6, 2025 | Fri 5–9:30 PM, Sat 9:30 AM–4 PM
Where: Main Street South, 36 Main Street S, Bethlehem, CT
Just a short drive from Woodbury, Bethlehem transforms into “Christmas Town” with a festive celebration featuring a tree lighting, live entertainment, craft and food vendors and children’s activities. The event is run entirely by volunteers and supports the historic Memorial Hall, adding a meaningful community touch.
More info: christmastownfestival.com
Woodbury Christmas Craft Fair & Boutique
When: Saturday, Dec. 6, 2025 | 9:30 AM–3:30 PM
Where: Woodbury Middle School, 67 Washington Ave, Woodbury, CT
Browse the 40th Annual Christmas Craft Fair & Boutique, featuring hand-crafted and unique merchandise from a curated group of vendors. From jewelry and décor to seasonal gifts, it’s an easy place to check off your list while supporting local artisans and community groups.
More info: skybluedesigns.com/event
Open House & Holiday Shoppe
When: Saturday, Dec. 6, 2025 | 11 AM–3 PM
Where: Glebe House Museum & Gertrude Jekyll Garden, 49 Hollow Rd, Woodbury, CT
Tour the beautifully holiday-decorated Glebe House, learn about its history – all while browsing their holiday shoppe filled with seasonal gifts and goodies. Vintage, handmade and new items will be available. Admission is free (donations accepted), making this a great low-key daytime outing to pair with other Woodbury holiday events.
More info: glebehousemuseum.org
Southbury “Be the Light” Holiday Celebration
When: Saturday, Dec. 6, 2025 | 4–7 PM (sensory-friendly hour 5–6 PM)
Where: Firehouse & Town Hall Green, 501 Main St S, Southbury, CT
Enjoy a free, family-friendly evening with crafts, games, cookie decorating, food trucks and a winter-scene photo booth on the Town Hall Green. A dedicated sensory-friendly hour ensures a welcoming experience for guests who need a quieter environment while still enjoying the festivities.
More info: southbury-ct.org/park-rec/events
TheatreWorks New Milford – “What the Dickens”
When: Select evenings December 4 – 21, 2025 | 8:00 PM (2:00 PM matinee available December 21)
Where: TheatreWorks, 5 Brookside Avenue, New Milford, CT
Just down the road in New Milford, this comedic homage to A Christmas Carol follows community theater actors attempting to perform the classic entirely from memory. Hilarious mishaps often ensue, making it a lighthearted seasonal performance.
More info: theatreworks.us/show/what-the-dickens-2025
Northern Lights Limited Train Ride
When: Select evenings November 22 – December 23, 2025 (after December 3) | Times vary; see website for available timeslots
Where: Railroad Museum of New England, 242 East Main Street, Thomaston, CT
In nearby Thomaston, this illuminated evening excursion takes passengers through a winter wonderland en route to the “North Pole.” Riders meet Santa and Mrs. Claus, sing carols with elves and enjoy festive cheer. Most magical of all, each child receives a special gift from Santa’s toy bag.
More info: rmne.org/excursions/northern-lights-limited
Enjoy the season, make a few memories close to home and have a happy holiday, Woodbury!
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