Seasonal & Holidays
12 Days Of Cheer In Middletown: Making This A December To Remember
Celebrate the season all month long with local lights, cozy stops, markets and hometown holiday charm.
The holiday season is officially here, and there’s no shortage of ways to soak up the magic in and around Middletown. 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 Middletown 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. Celebrate the ‘Magic of Middletown’ at the 40th Annual Holiday on Main Street.
Downtown comes alive each weekend from Thanksgiving to Christmas during the Holiday on Main Street festivities. Highlights of this year’s “Magic of Middletown” festivities include the Nov. 28 tree lighting, the Nov. 29 Holiday Pop-up Vendor Fair, North Pole Comes to Middletown Day on Dec. 6 a decorated vehicle parade and pub crawl on Dec. 12, and Paws & Claus Day on Dec. 13. Families can also drop letters into Santa’s Mailbox outside the Middlesex Chamber between Nov. 26 and Dec. 15. Keep an eye on the Holiday on Main Street website and Facebook page for the most up-to-date information, including any weather-related changes.
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2. ‘Come back to life’ with a handcrafted roast from Perkatory Coffee Roasters.
Just steps from downtown, Perkatory Coffee Roasters offers small-batch, artisan roasted coffee rooted in Middletown’s independent creative spirit. Their rotating single-origin lineup and signature blends are roasted with a hands-on approach that brings out distinctive flavors in every cup. Swing by to grab something warm before continuing your holiday errands or Main Street strolls.
3. Enjoy an elegant winter meal at Esca Restaurant & Wine Bar.
Located at the corner of Main and Washington, Esca Restaurant & Wine Bar blends traditional Italian cuisine with a contemporary, fine-dining ambiance. Seasonal entrées like pan-roasted duck breast, braised short ribs and Esca’s signature paella make it a festive choice for a holiday dinner or a refined night out. With extended hours seven days a week, it’s easy to plan a visit that fits your schedule; reservations are available on Toast.
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4. Hit the ice at Champions Skating Center.
Less than 10 minutes from Middletown, Champions Skating Center offers public skating on NHL- and Olympic-sized rinks, plus special themed events through the season. Highlights include the Nov. 29 Thanksgiving Skate, Dec. 6 Jersey Day and Dec. 20 Christmas Skate. Admission, skate rentals and pushers are available for all ages 4 and up; online pre-purchase is encouraged for a faster check-in. Public skate times vary, so checking the live schedule is essential before heading out.
5. Meet Santa and explore Santa’s Flight Academy at Westfarms.
About 35 minutes from town, Santa’s Flight Academy at Westfarms offers an interactive holiday experience for the family through Dec. 24. Families can book a time to meet Santa for photos before stepping into an immersive adventure featuring his 22-foot-tall sleigh. Reservations are recommended, though walk-ups are welcome as availability allows.
6. Explore the Fantasy of Lights at Lighthouse Point Park.
If you're spending time in the New Haven area this season, Fantasy of Lights at Lighthouse Point Park makes a great add-on to your visit. About 45 minutes from Middletown, the drive-through display fills the shoreline route with animated figures, light tunnels and colorful holiday scenes. This long-running tradition operates through Dec. 31 and remains a favorite for families who prefer to enjoy holiday lights from the warmth of their car. Admission is $10 per car or family van, $25 for minibuses and $50 for full-size buses; proceeds support Goodwill of Southern New England.
7. Take a brisk winter hike at Sleeping Giant State Park.
Less than half an hour from Middletown, Sleeping Giant State Park offers peaceful winter scenery for an invigorating walk, from quiet woodland trails to sweeping views from the observation tower. The park is open daily from 8 a.m. to sunset, and in-state registered vehicles can enter the park for free—so bundle up, bring a warm drink and enjoy one of Connecticut’s most iconic natural beauties.8. Cozy up for virtual Bedtime Stories with Mrs. Claus.
The virtual Bedtime Stories with Mrs Claus series, hosted by Branford Parks & Recreation, brings the magic of the North Pole straight to your home—and it’s completely free. Each week in December, you’ll receive a new video in your inbox, featuring Mrs. Claus reading a festive bedtime tale. Her gentle storytelling and cheerful holiday spirit make this a cozy, low-stress addition to the season.9. Spend an afternoon exploring Winterfest at Powder Ridge Mountain Park & Resort.
Just a short drive from Middletown, Powder Ridge Mountain Park & Resort hosts Winterfest on weekends from Nov. 28 through Dec. 21. General admission grants access to snow play areas, Santa visits, live music, an artisan market, an ice bar and more. Snow tubing tickets include all Winterfest activities plus a designated tubing session time. Event hours and offerings vary, so check the Winterfest schedule in advance to plan your perfect visit.10. Enjoy Hartford Stage’s production of A Christmas Carol: A Ghost Story of Christmas.
If you’re headed into Hartford, catch a live performance of A Christmas Carol: A Ghost Story of Christmas, running through Dec. 28. This spirited adaptation follows Ebenezer Scrooge’s Christmas Eve transformation through visits from the ghosts of Christmas Past, Present and Future, blending theatrical magic, haunting effects and heartfelt moments. The show runs approximately two hours with a 20-minute intermission and includes fog, haze, strobe lights and spooky ghosts; performances often sell quickly, so get your tickets online in advance!11. Cruise through the Magic of Lights.
A 30-minute drive brings you to Magic of Lights at Pratt & Whitney Stadium in East Hartford, running from Nov. 26 through Jan. 3. This drive-through display features LED-lit holiday scenes and animated characters set along a winding route. Tickets are valid anytime within the purchased time frame, with both standard tickets and season passes available online.
