By Jen Matteis

Think Madison slows down in the winter? Think again. As the temperature drops, downtown Madison heats up with exclusive shopping nights, eclectic craft fairs, and fun holiday events like the Turkey Trot and Tree Lighting. Spend the day taking in the festive holiday ambiance downtown, then retire to one of the town’s spectacular bed and breakfasts. From shopping to family fun, fairs and festivities, and B&Bs with unsurpassed luxury—it’s all right here in Madison.

Bargains Await
“We thought it would be a good early kick-off for holiday shopping,” says Madison Chamber of Commerce Executive Director Eileen Banisch of the upcoming Girls’ Night Out event. Held on Thursday, Nov. 10, Girls’ Night Out is sponsored in part by the Chamber and organized by Erica Tannen of Erica’s e-list—a self-described “excruciatingly opinionated guide to the Connecticut Shoreline.”

“She’s known for organizing these fun shopping events,” Banisch said of Tannen. “We’ve done two previous ones. It’s a good way to get out with your friends and get a head start on holiday shopping.”

The free event begins at 5 p.m. with half-priced wine at Cafe Allegre. Participants get a map of participating merchants and set off for some serious shopping—with 20 percent off their total purchase or an item at every store.
Ladies’ Shopping Night, or “Sip, Shop, and Save”—this year held on Thursday, Dec. 1—shares a similar format, kicking off with half-price wine and maps at Cafe Allegre. The stores don’t necessarily give 20 percent off, but there are bargains to be had.
Both events create a festive atmosphere in the downtown.

“Almost all the stores will have refreshments: wine, tea, coffee, cookies, crackers and cheese,” Banisch said. “It’s kind of like a party in all the stores.”

Finally, don’t forget to get out and support your small local businesses and find even more bargains on Small Business Saturday, Nov. 26. Held each year on the Saturday after Thanksgiving, the Chamber-supported event was started by American Express as a way to ensure support for small businesses, which can be overshadowed by Black Friday deals at the chain stores.
As Banisch explained, “It’s a way for the small businesses to say, ‘Look, we know everybody’s going to go to Walmart and Macy’s on Black Friday, but we want to bring everyone back and support the small businesses that are here year-round.”
Whether you’re a serious shopper or just looking to browse, don’t miss these three chances to explore downtown Madison decked out in its holiday décor.

Holiday Spirit
For 37 years, the Madison Jaycees has hosted the Turkey Trot on Thanksgiving Day. This year, construction at Hammonasset State Park means a change in venue: it will begin and end on the Madison Green, starting at 10 a.m. This fundraiser for local charities includes a five-mile road race and a two-mile family fitness walk. Runners will also want to note that the Madison Rotary Club’s annual half-marathon, this year held on Sunday, Nov. 13, is moving to the Guilford Fairgrounds due to the state park construction.

On Friday, Dec. 2, the holidays kick into high gear with the town’s Tree Lighting on the Green. Then, on Sunday, Dec. 4, Santa visits with local children on the porch of Cafe Allegre starting at 2 p.m. Holiday events will continue throughout the downtown: a performance by Daniel Hand High School’s group Encore, hot cocoa, story telling, and more.

“The day ends with the ABC annual concert at the Congregational Church,” Banisch added.
Children can also interact with the jolly man in the red suit through letters to Santa offered through the Women’s Club of Madison and the Madison Jaycees’ phone calls from Santa.

Finally, craft fairs abound throughout the entire holiday season at local churches including St. Margaret’s, St. Andrew’s, the Lutheran Church, the Congregational Church, and more. While stopping by one of the many craft fairs or browsing a display at the downtown merchants, consider picking up one additional item for a child in need. “There’s always a toy drive conducted by the police department,” noted Banisch. After all, it’s the season of giving—and some need a little bit more than most.

Places to Stay
The Grandfield
14 Stanton Court
Set on 3.5-acres across from Hammonasset, the Grandfield is a birdwatcher’s paradise and the newest B&B in town

Madison Beach Hotel
94 West Wharf Road
This luxurious resort overlooking Long Island Sound features a full-service spa, popular restaurant The Wharf, and more

Scranton Seahorse Inn
818 Boston Post Road
Experience traditional New England ambiance and luxurious accommodations in this charming inn set in an 1833 Greek revival home

Tidewater Inn
949 Boston Post Road
An elegant bed and breakfast surrounded by an English garden, located three miles from Hammonasset Beach

Cristy’s Madison
73 West Wharf Road

Cafe Allegre
725 Boston Post Road