Prepare for a holiday adventure in Westport! Our guide has all the exciting festive events. For those who know Westport's rhythm and those just learning its beat, our guide orchestrates holiday harmony.
One of the highlights of the season is the enchanting Winter Market, where local artisans showcase their crafts and visitors can enjoy festive treats while supporting the community. The delightful "A Sherlock Carol" offers a unique twist on the classic tale, blending mystery and holiday spirit with live performances. And the beloved Holly Days celebration features family-friendly activities and cheerful decorations that fill the town with festive joy. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Westport
- Holly Days
- Winter Market
- A Sherlock Carol
- Santa Express (Thomaston)
- All Aboard the Snow Clipper (Danbury)
- Spooky Suzuki Halloween Festival
- Clothing Tag Sale Fundraiser
- Annual Street Festival (East Lyme)
- Craft Fair on the Guilford Green (Guilford)
- Garlic & Harvest Festival (Bethlehem)
See these and even more events listed below!
Westport Holiday Markets and Shopping
Holly Days
What to Expect:
Interactive holiday activities with local vendors and Santa.
Description:
Holly Days at the Westport Museum for History and Culture features a gingerbread village, local vendor booths, a warming fire, and hot chocolate. Visit Santa and get a photograph, or book a hand-cut silhouette crafted right before your eyes.
Where: Westport | More Info: Holly Days
Winter Market
What to Expect:
Local artisans showcase a variety of handcrafted items.
Description:
The Westport Christmas Market in Kansas City offers a curated selection of unique gifts from local makers, live music, and seasonal treats. Visitors can explore historic streets filled with vendors selling handmade crafts, jewelry, clothing, and more.
Where: Westport | More Info: Winter Market
Craft Fair on the Guilford Green
What to Expect:
Showcase of over 170 independent craftspeople and makers.
Description:
The Craft Expo on Guilford Green features over 170 talented artists showcasing unique, high-quality handmade works in various media, including pottery, jewelry, textiles, and woodwork. Enjoy gourmet food and beverage tastings, live music, and family-friendly activities like a family art tent and kids' scavenger hunt. This event supports the Guilford Art Center's mission to provide accessible arts experiences.
Where: Guilford | More Info: Craft Fair on the Guilford Green
Westport Holiday Shows and Entertainment
A Sherlock Carol
What to Expect:
Sherlock Holmes investigates Ebenezer Scrooge's death on Christmas Eve.
Description:
A Sherlock Carol is a holiday comedy where Sherlock Holmes investigates the death of Ebenezer Scrooge on a dark and treacherous Christmas Eve. This clever, crowd-pleasing production features the Great Detective using his gifts to solve a Dickensian mystery, overcoming his own ghosts to crack the case. Recommended for ages 7 and up, it is a heartwarming and highly theatrical treat for all ages.
Where: Westport | More Info: A Sherlock Carol
Westport Holiday Giving Opportunities
Clothing Tag Sale Fundraiser
What to Expect:
Community-driven clothing sale benefiting Fairfield County non-profits.
Description:
The Westport Woman's Club hosts a Clothing Tag Sale Fundraiser featuring gently used women's, men's, and children's clothing and accessories. Donations support community grants and local charities.
Where: Westport | More Info: Clothing Tag Sale Fundraiser
Westport Other Holiday Activities
Spooky Suzuki Halloween Festival
What to Expect:
Family-friendly Halloween event with live music and activities.
Description:
The Spooky Suzuki Halloween Festival at Gilbertie's Herb Garden Center features a children's concert by Suzuki Music Schools, pumpkin patch, hay rides, and fun children's games like pumpkin bowling and witch hat ring toss. Vivace will perform as you arrive, and there are prizes for the best costume.
Where: Westport | More Info: Spooky Suzuki Halloween Festival
Santa Express
What to Expect:
Seasonally decorated train with visits from Santa and his elves.
Description:
The Santa Express is an afternoon train ride where families can visit Santa Claus and his elves. Passengers enjoy comfortable seating in restored New England Railroad cars, visit Santa for hand-delivered gifts, and participate in Christmas carol singing. Each child receives a special gift from Santa's toy bag.
Where: Thomaston | More Info: Santa Express
All Aboard the Snow Clipper
What to Expect:
Personalized gift-giving experience with Santa and Mrs. Claus.
Description:
All aboard the Snow Clipper for a personalized gift-giving experience with Santa and Mrs. Claus. Enjoy the museum interior, a short train ride, and a festive meet-and-greet with hot chocolate and treats.
Where: Danbury | More Info: All Aboard the Snow Clipper
Annual Street Festival
What to Expect:
Unique blend of community vendors, live music, and fireworks.
Description:
Celebrate East Lyme is an annual street festival in Niantic, CT, featuring over 200 vendors, live music, and a spectacular fireworks display over Niantic Bay.
Where: East Lyme | More Info: Annual Street Festival
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- East Norwalk (3 miles)
- Fairfield (5 miles)
- Darien (7 miles)
- Bridgeport (9 miles)
- North Stamford (10 miles)
- Trumbull (11 miles)
- Stamford (11 miles)
- Stratford (12 miles)
- Milford (17 miles)
- Danbury (18 miles)
- Shelton (18 miles)
- East Northport (18 miles)
- Port Chester (19 miles)
- Huntington Station (20 miles)
- Commack (21 miles)
- Smithtown (21 miles)
- Harrison (22 miles)
- White Plains (22 miles)
- Hauppauge (23 miles)
- Dix Hills (23 miles)
- Centereach (24 miles)
- Glen Cove (24 miles)
- Lake Ronkonkoma (24 miles)
- New Haven (25 miles)
- Brentwood (26 miles)
- Central Islip (26 miles)
- Plainview (26 miles)
- Ossining (26 miles)
- Deer Park (26 miles)
- Greenburgh (26 miles)
- Coram (26 miles)
- Holbrook (27 miles)
- East Haven (27 miles)
- Hicksville (27 miles)
- Naugatuck (29 miles)
- Medford (29 miles)
- West Babylon (29 miles)
- Bay Shore (29 miles)
- Mount Vernon (30 miles)
- Hamden (30 miles)
- Branford (30 miles)
- West Islip (30 miles)
- Wakefield (31 miles)
- Peekskill (31 miles)
- North Haven (31 miles)
- East Meadow (31 miles)
- Lindenhurst (31 miles)
- Yonkers (32 miles)
- Copiague (32 miles)
- East Patchogue (32 miles)
- Garden City (32 miles)
- Massapequa (32 miles)
- Throgs Neck (33 miles)
- Uniondale (33 miles)
- New City (33 miles)
- Waterbury (33 miles)
- Hempstead (33 miles)
- Van Nest (33 miles)
- The Bronx (33 miles)
- Parkchester (34 miles)
- Unionport (34 miles)
- Bayside (34 miles)
- Kings Bridge (34 miles)
- Whitestone (34 miles)
- Cheshire (34 miles)
- Fordham (34 miles)
- Franklin Square (34 miles)
- East Tremont (35 miles)
- Merrick (35 miles)
- University Heights (35 miles)
- Shirley (35 miles)
- Queens Village (35 miles)
- Tremont (35 miles)
- College Point (35 miles)
- Freeport (35 miles)
- Morris Heights (36 miles)
- Hunts Point (36 miles)
- Elmont (36 miles)
- Spring Valley (36 miles)
- Morrisania (36 miles)
- Baldwin (36 miles)
- Fresh Meadows (36 miles)
- Melrose (36 miles)
- Washington Heights (36 miles)
- Englewood (36 miles)
- Bergenfield (36 miles)
- Hollis (36 miles)
- Rockville Centre (36 miles)
- Guilford (37 miles)
- Cambria Heights (37 miles)
- East Elmhurst (37 miles)
- Mott Haven (37 miles)
- Kew Gardens Hills (37 miles)
- Hillside (37 miles)
- Valley Stream (38 miles)
- Fort Lee (38 miles)
- Oceanside (38 miles)
- Corona (38 miles)
- Teaneck (38 miles)
- Briarwood (38 miles)
- Jackson Heights (38 miles)
- Harlem (38 miles)
- Laurelton (38 miles)
- Rosedale (39 miles)
- Rego Park (39 miles)
- East Harlem (39 miles)
- Jamaica (39 miles)
- Morningside Heights (39 miles)
- Elmhurst (39 miles)
- Forest Hills (39 miles)
- Palisades Park (39 miles)
- Springfield Gardens (39 miles)
- Richmond Hill (39 miles)
- Astoria (39 miles)
- Woodside (40 miles)
- Meriden (40 miles)
- Cliffside Park (40 miles)
- Paramus (40 miles)
- Hackensack (40 miles)
- Middle Village (40 miles)
- Manhattan (40 miles)
- Queens (40 miles)
- South Ozone Park (41 miles)
- Woodhaven (41 miles)
- Maspeth (41 miles)
- Ozone Park (41 miles)
- Sunnyside (41 miles)
- Glendale (41 miles)
- Mahwah (41 miles)
- Ridgewood (41 miles)
- Long Island City (41 miles)
- Long Beach (41 miles)
- North Bergen (41 miles)
- Howard Beach (42 miles)
- Ridgewood (42 miles)
- Lodi (42 miles)
- Hell's Kitchen (42 miles)
- West New York (42 miles)
- Newburgh (42 miles)
- Bristol (42 miles)
- Greenpoint (42 miles)
- Far Rockaway (42 miles)
- Cypress Hills (42 miles)
- Bushwick (43 miles)
- Fair Lawn (43 miles)
- East New York (43 miles)
- Union City (43 miles)
- Williamsburg (43 miles)
- Elmwood Park (43 miles)
- Gramercy Park (43 miles)
- Garfield (43 miles)
- East Village (43 miles)
- Kiryas Joel (44 miles)
- Brownsville (44 miles)
- Chinatown (44 miles)
- Canarsie (45 miles)
- Hoboken (45 miles)
- Passaic (45 miles)
- New York City (45 miles)