Don't miss the best holiday highlights in Cheshire! Our guide features all the must-see events and activities. From Cheshire residents to wandering spirits, this guide ensures you catch every moment of seasonal magic.
Popular Events: Experience the charm of the Stonington Holiday Stroll & Marketplace, where local artisans showcase their crafts amid festive decorations. Then, enjoy the spirited atmosphere of Guilford Holiday Fest, featuring enchanting lights and delightful treats. And the Norwich Winterfest & Christmas Market is something you definitely don't want to miss, offering a blend of unique gifts and seasonal cheer. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Cheshire
- Stonington Holiday Stroll & Marketplace (Stonington)
- Guilford Holiday Fest (Guilford)
- Norwich Winterfest & Christmas Market (Norwich)
- Santa Express (Thomaston)
- All Aboard the Snow Clipper (Danbury)
- Elf the Musical (Hartford)
- A Christmas Carol (Hartford)
- Cove Ledge's Holiday Market (Stonington)
See these and even more events listed below!
Cheshire Holiday Markets and Shopping
Guilford Holiday Fest
What to Expect:
Unique gifts from hundreds of American artists.
Description:
The Guilford Art Center's Holiday Expo 2024 offers a diverse selection of handcrafted holiday gifts from hundreds of American artists, makers, and designers. The event features a wide range of items, including accessories, candles, ceramics, clothing, fiber art, glassware, homewares, jewelry, leather goods, Christmas ornaments, soaps, specialty foods, and stationery. New items are added throughout the season, providing visitors with the opportunity to discover fresh finds.
Where: Guilford | More Info: Guilford Holiday Fest
Norwich Winterfest & Christmas Market
What to Expect:
Twinkling lights, festive music, and seasonal treats.
Description:
Norwich Winterfest & Christmas Market offers a variety of stalls selling handmade crafts, unique gifts, and delicious seasonal treats. The event features live performances, fun rides, and the opportunity to meet Santa Claus.
Where: Norwich | More Info: Norwich Winterfest & Christmas Market
Cove Ledge's Holiday Market
What to Expect:
Local artists and artisans selling handmade goods.
Description:
Cove Ledge's Holiday Market features local artists and artisans selling handmade goods and seasonal items in a charming outdoor setting.
Where: Stonington | More Info: Cove Ledge's Holiday Market
Cheshire Holiday Shows and Entertainment
Elf the Musical
What to Expect:
Delightful characters and catchy songs by a talented 12-piece live band.
Description:
Elf the Musical is a heart-warming and hilarious tale of Buddy the Elf, who leaves the North Pole to find his real father in New York City. Featuring delightful characters and catchy songs performed by a talented 12-piece live band, this show is guaranteed to put you in the Christmas spirit.
Where: Hartford | More Info: Elf the Musical
A Christmas Carol
What to Expect:
Ebenezer Scrooge's redemption through supernatural visitations.
Description:
A classic adaptation of Charles Dickens's "A Christmas Carol" by Hartford Stage, directed by Michael Wilson, featuring Ebenezer Scrooge's transformative journey with the ghosts of Christmas Past, Present, and Future.
Where: Hartford | More Info: A Christmas Carol
Cheshire Other Holiday Activities
Stonington Holiday Stroll & Marketplace
What to Expect:
Community carol singing and competitive holiday window displays.
Description:
The Stonington Holiday Stroll & Marketplace is an annual event featuring a tree lighting ceremony, community carol singing, and a special visit by Santa. Following the tree lighting, participants can enjoy a holiday stroll down Water Street, where local merchants keep their shops open late and compete for the best window decorations in the Borough A-Glow contest.
Where: Stonington | More Info: Stonington Holiday Stroll & Marketplace
Santa Express
What to Expect:
Seasonal train ride with Santa and festive treats.
Description:
The Santa Express is an afternoon train ride where parents and kids can visit Santa Claus and his elves. Each child receives a special gift from Santa's toy bag, and the train is decorated seasonally inside and out. The journey includes visits with Santa and Mrs. Claus, hot chocolate, and festive treats.
Where: Thomaston | More Info: Santa Express
All Aboard the Snow Clipper
What to Expect:
Personalized gift-giving experience with Santa and Mrs. Claus.
Description:
At the Danbury Railway Museum, join All Aboard the Snow Clipper for a personalized gift-giving experience. Enjoy the museum's interior, including a Letters to Santa coloring station and operating model railroads. Take a short train ride through historic Danbury Railyard and meet Santa and Mrs. Claus for the first gifts of Christmas. Afterward, stroll through the railyard with hot chocolate and marshmallows.
Where: Danbury | More Info: All Aboard the Snow Clipper
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Meriden (6 miles)
- Hamden (7 miles)
- North Haven (8 miles)
- Naugatuck (8 miles)
- Waterbury (9 miles)
- Bristol (12 miles)
- New Britain (13 miles)
- New Haven (13 miles)
- Middletown (14 miles)
- East Haven (15 miles)
- Farmington (16 miles)
- Branford (16 miles)
- Shelton (16 miles)
- Newington (17 miles)
- Guilford (18 miles)
- Wethersfield (20 miles)
- West Hartford (20 miles)
- Milford (21 miles)
- Glastonbury (21 miles)
- Hartford (21 miles)
- Trumbull (24 miles)
- Torrington (24 miles)
- Bloomfield (24 miles)
- East Hartford (25 miles)
- Stratford (25 miles)
- West Torrington (25 miles)
- South Windsor (27 miles)
- Bridgeport (27 miles)
- Manchester (27 miles)
- Windsor (28 miles)
- Danbury (30 miles)
- Fairfield (31 miles)
- Westport (34 miles)
- Enfield (37 miles)
- East Norwalk (37 miles)
- Montville Center (39 miles)
- Mansfield City (39 miles)
- Windham (41 miles)
- Darien (41 miles)
- North Stamford (42 miles)
- Agawam (42 miles)
- New London (43 miles)
- Norwich (43 miles)
- Coram (44 miles)
- Westfield (44 miles)
- West Springfield (44 miles)
- Springfield (45 miles)