12 Days Of Cheer In Madison: Making This A December To Remember

The holiday season is officially here, and there’s no shortage of ways to soak up the magic in and around Madison. To help get you in the spirit, we’ve rounded up a dozen festive ideas you can enjoy throughout the month — each one a fun, joyful way to celebrate the season close to home.

From twinkling light displays and holiday markets to cozy treats, local shopping spots, winter activities and seasonal shows, these 12 picks highlight what makes Madison feel especially merry this time of year. Whether you check off one or all twelve, it’s all about slowing down, supporting local businesses and making memories.

1. Sip coffees and find thoughtful gifts at Willoughby’s Coffee & Tea.

Willoughby’s Coffee & Tea has been roasting small-batch beans since 1985, building its reputation on precision, freshness and sourcing that reflects decades of expertise. Holiday visitors can browse an extensive lineup of single-origin coffees and curated tea selections ideal for cold-weather brewing. Gift certificates and boxed coffee sets are also available, offering the perfect presents for caffeine lovers while checking a few items off your holiday list.

2. Browse books and holiday gifts at RJ Julia Booksellers.

RJ Julia Booksellers has been a staple in downtown Madison for more than 35 years, known for its passionate staff, hand-picked selections and shelves filled with stories waiting to be discovered. Winter shoppers will find award-winning book recommendations, literary gifts and frequent author events that bring readers together throughout the season. The store’s inviting layout and knowledgeable booksellers make it a standout stop for anyone looking to uncover new titles or purchase meaningful holiday presents.

3. Enjoy locally sourced winter comfort food at Fat Duck Tavern.

Fat Duck Tavern builds its menu around premium meats from ranches and farms known for quality and sustainable practices, creating cold-weather dishes with depth and character. Guests can warm up with steaks from DemKota Ranch Beef, rich Duroc pork from Compart Family Farms or grass-fed burgers crafted with Joyce Farms beef. The focus on thoughtful sourcing gives the tavern’s seasonal offerings a cozy, hearty feel well-suited to December evenings.

4. Stop in for seasonal pastries at S&B Cafe.

S&B Cafe offers a welcoming spot for a relaxed winter meal, with a menu that ranges from homemade pastries to comfort-food favorites and globally inspired dishes. Seasonal treats like their mini orange cheesecakes add a festive touch, and diners can pair them with a warm drink on chilly days. The café’s casual atmosphere makes it a reliable choice for a laid-back holiday-season breakfast or lunch.

5. Enjoy storytime magic with Mrs. Claus at home.

This December, Branford Parks & Recreation brings back its virtual Bedtime Stories with Mrs. Claus series, offering families an easy way to add a little holiday magic at home. After registering, participants receive weekly video storytimes throughout the month featuring cheerful, festive readings perfect for winding down the night. The format makes it simple to follow along at your own pace, creating a no-stress tradition kids can look forward to each week.

6. Gather for Santa’s pancake breakfast at The Shore Line Trolley Museum.

Just minutes from Madison, the Shore Line Trolley Museum hosts its festive pancake breakfasts with Santa on select December Saturdays. Families enjoy a warm meal before Santa visits each table, adding fun photo moments for little ones. Afterward, guests board a vintage trolley for a narrated ride along the museum’s historic tracks and winter scenery, with seating available at 8:30 and 9:30 a.m.

7. Settle in for classic French comfort dishes at Bar Bouchée.

Bar Bouchée brings the spirit of a traditional Lyon-style bouchon to Madison, offering rustic French comfort food in a lively, intimate setting. Regulars gather at the zinc bar for cocktails and conversation, while the dining room fills with the aroma of bistro favorites that suit the cold-weather season. Gift cards are also available for those looking to share a local dining favorite during the holidays.

8. Explore festive deals and treats at The Shops at Yale.

About 25 minutes from Madison, The Shops at Yale celebrate the season with holiday promotions and free public events throughout the month. Shoppers who spend $50 or more at participating retailers can redeem their receipt for a complimentary gourmet hot cocoa or cookie, adding a sweet touch to winter errands. Plus, visitors can get free two-hour parking in select lots through Dec. 24, allowing you to take your time exploring the Chapel Street and Broadway districts.

9. Visit Santa for holiday photos at Connecticut Post Mall.

10. Explore downtown festivities during New London’s holiday celebration.

New London’s waterfront district comes alive in December during its Holiday Celebration, featuring community events, shopping specials and festive performances that highlight the city’s diverse holiday traditions. Visitors can browse small-business promotions, catch live music along Bank Street or stop into local galleries hosting seasonal art shows. Families can also enjoy activities like the Santa Shopping Stroll, complete with maps, treats and giveaways from participating businesses.

11. Cruise through a dazzling show at Fantasy of Lights.

Families who don’t mind a quick 30-minute trip to New Haven can enjoy Fantasy of Lights, a long-running holiday tradition that fills Lighthouse Point Park with colorful displays and animated light scenes. The route winds past glowing tunnels, oversized characters and dozens of holiday setups that can all be enjoyed from inside a warm car. The show operates nightly through Dec. 31, with hours from 5:00–9:00 p.m. Sunday through Thursday and extended to 10:00 p.m. on Fridays and Saturdays. Admission is $10 per car or family van, $25 for minibuses and $50 for full-size buses, and all proceeds benefit Goodwill of Southern New England.

12. Take in the shimmering displays at Hubbard Park’s Festival of Silver Lights.

About 30 minutes away in Meriden, Hubbard Park becomes a winter spectacle in December for its Festival of Silver Lights, featuring more than 300,000 lights arranged around the lake, hillside and wooded paths. Visitors can drive the loop for a glowing nighttime view or park and walk portions of the display for an up-close look at the illuminated scenes. The lights remain up through Dec. 31, offering a free and memorable outing throughout the holiday season.

Stay warm, shop local and enjoy every twinkling moment — happy holidays, Madison!