The annual Chili Cook-off returns to Cromwell of Saturday December 7 from 5-8pm. There are CASH prizes for the best batches of chili plus the holiday block party and tree lighting. https://heatherpolke.wufoo.com/forms/q4twnn81ik2fhg

Business Owners of Black Rock is hosting its first annual Holiday Shop & Stroll on Sunday December 8, right before the annual Black Rock Community Council tree lighting. Support local Black Rock businesses while enjoying music, snacks, and drinks.

The Greenwich Holiday Stroll spans a whole weekend and takes place on December 7 & 8. Enjoy fun festivities for the whole family throughout downtown Greenwich, Byram, Cos Cob and Riverside. This year will have over 110 vendors as well as activities like photos with Santa. https://www.greenwichreindeerfestival.com/greenwich-holiday-stroll

Tavern on State presents a Winter Game themed Sunday Supper on December 8. 5 courses with wine pairings costs $85 per person.

Red Bee Honey's Holiday Open House returns on Sunday December 8 from 11am-4pm. Shop Local and Shop Small at Red Bee Honey and pick up your holiday honeys, gift boxes, beeswax candles, soap and many other goodies. Tour a working apiary and meet author and founder, Carla Marina Marchese who will be signing copies of her books. Other local vendors and artists will be there as well with gourmet foods, crafts, and other items. https://www.facebook.com/events/356791105074763/

Half Full’s outdoor Winter Beer Garden is now open! Find it in Mill River Park's Winter Wonderland during the entire month of December with a space double the size of last year! The 203 is also there with a holiday inspired pop-up booth.

On Monday December 9, Buon Appetito Restaurant of Canton invites you to a Steele Wine Dinner. The meal includes 4 courses, dessert, and wine pairings. It costs $75 per person, plux tax and gratuity, and runs from 6:30-8:30pm. https://www.localwineevents.com/events/detail/769928

55 Wine Bar, Harry's Wine and Liquor Market, and VIAS Imports present this year's Annual Holiday Wine Dinner on Tuesday, December 10 at 7pm. Enjoy a carefully curated 6 course prix fixe menu paired with delicious wines. Tickets are $75 + tax and gratuity. Limited seating. Call the restaurant to reserve. https://55winebar.com/

On Wednesday December 11, join the Restaurant at Rowayton Seafood for a Halter Ranch Wine Dinner. The five course meal kicks off at 6:30pm and costs $95 plus tax and tip. https://www.facebook.com/marianne.mcnulty.1/posts/10220055082745182

Hartford Flavor Company and Wild Moon Liqueurs are teaming up for a Holiday Mixology Class on Wednesday December 11 from 6-7:30pm. Learn how to make, shake and mix up craft cocktails for the holiday season and beyond. Pizza will be served! Tickets are $40 per person. https://www.eventbrite.com/e/holiday-mixology-class-tickets-80300385615

It’s “all about the braise” on Thursday December 12. Ari Long is coming to Wakeman Town Farm to show us how to prepare leg of lamb and seasonal side dishes in time for the holidays. Don’t forget to BYOB! The class is limited to 16 so book your seats early. https://www.wakemantownfarm.org/

On Thursday December 12, attend a Toro Loco Pop Up Dinner Tasting hosted by Popovers Bistro in Simsbury. The event will offer a sneak peek of the soon to open Toro Loco restaurant and will include a three-course family style meal with Mexican & Spanish inspired  tapas. Tickets are $45 per person. https://www.brownpapertickets.com/event/4455941

The State Street Toys for Tots Pub Crawl kicks off at 12pm on Saturday December 14 at Cave a Vin! Enjoy drink specials and free snacks as you make your way to Christopher Martins, Oak Haven, Diesel, and JP Dempsey’s. Tickets are $25 and are available at statestreettoys2019.eventbrite.com.

Valencia Luncheria in Norwalk hosts an Ugly Sweater Christmas Brunch on Saturday December 14. how off your ugliest Christmas sweater to brunch at Valencia and receive a complimentary brunch punch or batido/jugo. Happy Holidays!

Sunday December 15 is Kids Day at Palmers Market in Darien. Stop by between 2 and 4pm for special kid activities including a scavenger hunt, cupcake decorating, a ride on Trevor the talking reindeer, and other fun holiday activities.

Jazz Brunches continue at the Wadsworth Atheneum Museum of Art on Sunday December 15. Enjoy a buffet brunch in the Untitled Bistro with live jazz by Charmagne Tripp. Tickets include museum admission, jazz, brunch, and one complimentary bloody mary or mimosa. There are two seatings, one at 10:30am & one at 12:30pm. Tickets are $39; $29 members. https://www.eventbrite.com/e/jazz-brunch-charmagne-tripp-tickets-79533449689

The Griswold Inn’s Holiday Bill of Fare has returned! The special seasonal menu features game offerings alongside classic Gris signature dishes. The meal will be served by costumed waitstaff while the Royal Court Singers perform. Call 860-767-1776 to reserve.