Dates for this event

Dec 6, 2025

Westport Winterfest

December 6  - December 6
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Here’s our Westport Winterfest schedule:

With Room for Surprises!

winterfest

8-4pm -Boy Scouts Tree & Wreath Sale on the Heritage House lawn 

8-2pm - Free Drinks at JAMBS courtesy of Chazy/Westport Communications

9am-4pm - Christmas Sale at the Ship’s Store at the Westport Marina

8-10:30am -Breakfast and Craft Sale, Westport Federated Church

8-10:30am - Donate your gently used women’s and men’s L and XL coats to the elderly at the Westport Federated Church during breakfast, or on the front porch of 6434 Main Street. Thank you!  

10-12pm-Cookie Decorating with Sandy Goodroe at Bradamant Realty

10-1pm - Temporary Tattoos with Caroline Vanderhoof at Ledge Hill Studio Downtown

10-2pm - Photos with Mr and Mrs Santa Claus cutouts at the Heritage House

10-2pm -Guest book signing / Indoor yard sale at the Heritage House 

10-2pm- Memory Tree ornament decorating at the Heritage House: proceeds to benefit the Westport EMS Squad.

10-2pm- Write letters to Santa, at the Library 

10-2pm- Kids Winter Coat Swap at the Library (Organized by Griffin Guardian Alliance)

10-5pm- Bessboro Shop Discount sale 

10-7pm-ish-K&D Snack Shack (In between JAMBS and the Bessboro Shop) open, serving warm sandwiches, cookies, Wassail (a traditional cider), hot cocoa and sodas. 

12pm - 12:30 pm - Lakeside School presents ‘The Elves and the Shoemaker”, a puppet show for young children, at the Mill.

12:30 pm - 1 pm - Lakeside School presents ‘The Elves and the Shoemaker”, a puppet show for young children, at the Mill.

11-1pm -Stories & Holiday craft making at the Library 

11-4pm- Hot soup, walking tacos, fresh baked treats served at the Ballard Park Skate Shack by Winton’s Tavern

12-3pm- ‘Meet & Greet’ at the new Westport business, the Finishing Stone - Sale of Stained glass items from Previous owner Kip, and meet the new owner, tour the space.

12-6pm- Homestead Spirits 10% off any purchase of $20 or more - all products 

1-3pm - Storytime with Sarah Von Rijsewijk from her new book, ‘Santa and the Sled Dogs’ at Snowfort Books

3:30pm-5:15pm - Movie ‘Polar Express’ viewing, with cocoa and cookies at the Library

4pm-8pm - the Mountain Dog Restaurant and Pub is open with holiday specials and treats!

5pm- 6:30 pm Food Shelf Drop off location at the Tree Lighting Ceremony, on the Library Lawn.

5pm-6pm - Flowers Plus! Penguin/Lottery Raffle drawing (by Santa) an hour before the arrival of Santa, Main Street Location TBD. (inflatable penguin and lottery tix!)

5pm - 8pm - Winton’s Tavern open for festive dinner and drinks! Bar open till 9pm.

5pm - 9pm - The Knock at the Mill is open for ingenious vegetarian fare and craft cocktails!

5:30pm - Tree lighting Ceremony & singing with Candy Cane Quartet. on the the Library Lawn
Thanks to the Bessboro Shop and Rolling Hills Estate Winery for sponsoring the Candy Cane Quartet!

5:30pm - Horse-drawn wagon rides and photo opportunity with Gabe from Windy Woods Pastures on the Library Lawn 

5:45pm - Santa Parade with Westport Fire Dept starts in Wadhams at 5:45 and arrives main street Westport by 6:00pm. Sponsored by the Westport Volunteer Fire Department.

6pm - 9 pm - JAMBS Beer and Wine open for fine beer, wine and great company!

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