12 Days Of Cheer In Stratford: 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 Stratford. 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 Stratford 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. Drive through the twinkling displays at Fantasy of Lights.

Fantasy of Lights at Lighthouse Point Park, about 30 minutes from Stratford, has been a favorite winter tradition for three decades, drawing families for its animated displays and festive glow. Running now through December 31, the drive-through opens nightly at 5:00 p.m., with later hours on weekends. It’s a simple, cozy way to enjoy the season — just pile into the car and roll through the lighted scenes. Admission starts at $10 per car, and all proceeds benefit Goodwill of Southern New England.

2. Spend an afternoon on the ice at Wonderland of Ice.

Just a short drive from Stratford, Bridgeport’s Wonderland of Ice offers daily public skating on two NHL-sized rinks, with plenty of space whether you’re practicing skills or just getting comfortable on the ice. Sessions cost $15, with skate rentals available for $5. They also have a pro shop and snack bar for quick warm-ups. Schedules vary by week, so check their homepage for current skate times.

3. Browse handmade finds at Winterfair in New Haven’s Union Station.

This year, Winterfair has taken over the upper level of New Haven’s Union Station with rotating vendors and a lively holiday atmosphere. Each Saturday and Sunday from 11:00 a.m. to 4:00 p.m., November 29 to December 21 (except December 7), you’ll find more than 30 makers on-site — part of a larger group of 100+ small and local businesses participating throughout the season. It’s an easy 25-minute trip and a fun way to pick up unique gifts you won’t see in big-box stores.

4. Grab a cozy drink (and bring your pup) to Frenchies Coffee Bar.

Frenchies Coffee Bar is a Stratford favorite for its friendly staff, cozy energy and the smell of Downeast Coffee Roasters’ small-batch beans as soon as you walk in. The pastries and croissants are reliably delicious, and the Cajun chicken sandwich is one of the menu items locals rave about. Dogs are welcome too — the “Doggy Nook” is stocked with treats so they can relax while you warm up. If you’re holiday shopping, consider grabbing a bag of their coffee as a stocking stuffer or bringing a friend here for a low-key catch-up during holiday break.

5. Curl up with a new book from Obodo Serendipity Books.

Tucked into the heart of Paradise Green, Obodo Serendipity Books offers a warm, welcoming space filled with diverse stories for readers of all ages — plus a friendly, dog-approved atmosphere. The shelves lean toward heartfelt, meaningful reads, and the shop regularly hosts author events, yoga classes and even Jazz Nights, giving it a lively community feel. Whether you’re browsing for a holiday gift or picking up a new read for the quieter stretch of winter, you’ll find plenty to linger over on a cold day. Check their website for upcoming events.

6. Get creative with a holiday workshop at The Giggling Pig in Milford.

Less than 20 minutes from Stratford, The Giggling Pig in Milford offers a place where kids and families can explore art together in a relaxed, encouraging setting. Their Walnut Beach location hosts a full lineup of seasonal classes — from family holiday paint parties to sweet-treat ornament workshops and sea-glass paint-and-sip events for adults. It’s a fun way to squeeze in a little creativity during the busy season and come home with something handmade. Check their events pages for the latest holiday offerings.

7. Hop aboard a holiday trolley for a Santa visit at the Shore Line Trolley Museum.

The 25-minute drive is worth it for the Shore Line Trolley Museum’s “Next Stop: Santa!” event, which runs on weekends through December 21 and offers a nostalgic holiday outing for all ages. Families board a heated, decorated trolley for a short ride to Santa, where kids can share their wish lists and receive a small gift. Afterward, you can warm up with hot chocolate, explore the museum’s holiday-themed trolleys and browse the gift shop for unique presents. Most of the experience takes place outdoors, so bundle up before heading over.

8. Experience a new holiday story with ‘Scrooge and Marley’ at The Legacy Theatre.

If you want something a little different from the usual A Christmas Carol productions, The Legacy Theatre’s Scrooge and Marley (December 3–14) follows Jacob Marley’s life before he became a ghost — how he met Scrooge, how their partnership formed and how one man’s choices shaped the other’s redemption. The run includes a mix of matinees and evening shows, with performances most days between December 3 and 14, including several 2:00 p.m. and 7:00 p.m. options throughout both weeks. About 30 minutes from Stratford, it’s warm, witty and family-appropriate for ages 8+. Showtimes and tickets are available on their website.

9. Enjoy soulful, seasonal Italian cooking at Biagio’s Osteria.

Biagio’s Osteria in Stratford is known for its thoughtful blend of classic and modern Italian cooking, built on organic, seasonal ingredients and a deep respect for tradition. Chef Biagio Barone honed his craft in Southern Italy, drawing inspiration from the dishes he grew up making with his family, and it shows in the menu’s fresh pastas, slow-simmered sauces and beautifully balanced entrées. With a warm dining room and an extensive wine list, it’s an inviting spot for a hearty winter meal or a holiday dinner out with friends.

10. Treat yourself to a sweet winter pick-me-up at Edible Couture.

With its stylish décor and the smell of fresh-baked cupcakes wafting through the space, Edible Couture is a sweet-tooth destination any time of year — but especially around the holidays. They’re known for small-batch desserts made with high-quality ingredients, including cupcakes, cookies and their crowd-favorite sweet potato cake. The space has a fun, fashion-inspired feel, and the staff is as warm as the aroma coming from the kitchen. It’s a great stop when you need something special for a holiday gathering or just want a little boxed-up joy to bring home on a cold day.

11. Catch a seasonal performance at the century-old Shubert Theatre.

Holiday performances take center stage at New Haven’s historic Shubert Theatre, just 25 minutes from Stratford. Opened in 1914, the Shubert still feels like a true Broadway house, with an intimate layout that makes every show feel close and full of energy. This season’s lineup includes Miracle on 34th Street the Musical, The Nutcracker, Ireland with Michael: A Celtic Christmas and several other festive performances. Head to their events page for the full schedule and ticket options.

12. Sip winter brews and enjoy holiday events at Two Roads Brewing Company.

Right in Stratford, Two Roads offers two side-by-side taprooms — the main brewery and Area Two Experimental Brewing — each with its own atmosphere, from family-friendly lounge seating to a bar area for 21+. You can settle in with a beer flight, grab cans to go for an easy holiday gift or step outside to the dog-friendly beer garden when the weather cooperates. December brings special events like a winter market and tree lighting, a “Most Wonderful Crime of the Year” murder mystery dinner and even brunch with Santa. Check their events page for the full seasonal lineup.

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

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