Thursday, December 2nd
- Ladies Night Shopping in Madison, hosted by the Madison Chamber of Commerce, from 5-8pm. Check in at the Cafe Allegre, 725 Boston Post Road between 5-6pm for a half price glass of cheer, then head out to our great stores to enjoy special sales, beverages & snacks! Visit the event page on Facebook for a full list of participating stores.
Friday, December 3rd
- First Friday, Starry Night, and Santa in Chester from 5-8pm. Join the Merchants of Chester for an extra special First Friday celebration! In addition to new exhibitions, exiting seasonal menus & ice cream flavors, live music and great shopping, the starts will be lit, all at once at 5:45pm!! Also, Chester Hose Company has invited SANTA to visit on his fire truck at 6:15 so make sure to tell him what’s on your wishlist this year! Come out to Main Street for this exciting event and stay for shopping and dinner. 5-8pm in the Village! If you would like to purchase a star for your home, please contact the artist, Christopher Owens, at chestercottagect.com
- Holiday Shopping Extravaganza at the Chester Meeting House from 5-9pm. Local artisans selling unique and handcrafted items. From home decor, jewelry, to one of a kind art, you will find something for everyone!
Saturday, December 4th
- Haddam/Killingworth Intermediate/Middle School PTO Craft Fair at Haddam Killingworth Middle School from 9am-3pm. Craft Fair featuring artists, crafters and makers from across Connecticut. Food trucks, Book Fair, and Day Raffle too! Masks will be required indoors.
- 26th Annual Holiday Craft Fair at the North Madison Congregational Church from 9am-2pm. There will be over 25 quality artisans and raffles. It’s the perfect place to find gifts for all your loved ones! There will also be homemade Turkey Pot Pie and Soups for sale that can be purchased per serving or take home the whole pie! Admission is Free!
- Saybrook Starry Night Festival from 9am-5:30pm to kick off celebrating the season! A day of festivities and fun activities to kick off the holidays! 5k run, story time, visits with Santa, tree lighting, and more! See the full schedule of events here.
- Story Time with the Grinch at the Westbrook Outlets from 12-3pm. Presented by Williams Sonoma OutletJoin us for hot chocolate, selfies & story time with the Grinch! 3 Time Slots: 12:15-1:00PM, 1:15-2:00PM, 2:15-3:00PM. Call Williams Sonoma to reserve your spot: 860-399-0195. Suggested Donation: $10 Per Child All Proceeds Go To St. Jude’s. Reservations are required & space is limited.
Sunday, December 5th
- Chester Holiday Market from 10am-1pm. Several vendors from the Chester Farmers Market (and some that are new for the Holiday Market) join in for the 4 Sundays between Thanksgiving and Christmas. You’ll find farmers on the sidewalks and special events and menus in the shops and restaurants. In addition Mrs. Clause will be strolling the Village, spreading holiday cheer!
- 2021 Holiday Bazaar at the Wadsworth Mansion in Middletown from 10am-3pm. Featured vendors from the Open Air Market will be selling their handmade products. Come and shop for the holidays! Enjoy lunch and hot beverages in the bar provided by David Alan Catering. $2.00 donation per adult for admission. Children are free! A full list of participating vendors can be found here.
- Holiday Open House and Artist Demonstration at Beach & Barn Furniture in Westbrook from 3-7pm. Sip and shop for unique one-of-a-kind holiday gifts and experience a live epoxy river table demonstration. Hand crafted charcuterie boards, cheese boards, wall hangings, driftwood centerpieces, and whales by Driftwood Design.