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.
11-7pm - 10% off any Christmas Centerpiece preorder, and free mini dried flower bouquet with any purchase at Vagabond Blooms!
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.
5:15pm - Hot Chocolate served at the Wadhams Free Library, (A sweet treat for everyone at the start of the parade!)
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
5:30pm - Pop-up Community Choir with the Candy Cane Quartet! Immediately following the tree lighting. All are welcome, no experience necessary. Optional rehearsal on Dec 6 from 9-10am. details at www.CandyCaneQuartet.com/Westport.
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!
See Below for memories of last year’s festival!
Winterfest 2025 Schedule, to be updated soon!
Memories from Winterfest 2024!
There are no upcoming events at this time.