Seasonal & Holidays
12 Days Of Cheer In Monroe: 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 Monroe. 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 Monroe 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. Follow the Light Up Monroe displays around town.
A longtime town tradition, Light Up Monroe brings neighbors together each December with creative, resident-made holiday displays. Homes switch on beginning Dec. 6, when public voting also opens, highlighting how different corners of Monroe celebrate the season. Keep an eye on the public Facebook group for participating addresses and updates as the displays go live.
Find out what's happening in Monroefor free with the latest updates from Patch.
2. Lace up for public skating at Wonderland of Ice.
Wonderland of Ice is a go-to winter activity for many local families, offering daily public skating just down the road from Monroe. The Bridgeport facility features two NHL-sized rinks, along with skate rentals, lessons and a pro shop for visitors who want to brush up their skills or simply spend time on the ice. Admission is $15 per session, with skate rentals available for $5. Check out the website before you go to confirm available hours, as session times can vary.
3. Pause for a warm drink at Last Drop Coffee Shop.
A welcoming stop on cold December days, Last Drop Coffee Shop on Main Street offers specialty drinks and simple, health-minded meals in a relaxed space lined with books. The women-owned café encourages visitors to slow down, whether they’re easing into the morning or breaking up a busy afternoon.
Find out what's happening in Monroefor free with the latest updates from Patch.
4. Explore local makers at Winterfair in New Haven.
If you’re headed into New Haven for shopping, stop by Winterfair, which brings rotating vendors to New Haven Union Station each weekend from Nov. 29 through Dec. 21. More than 30 makers participate each market day, representing over 100 small and diverse businesses throughout the season. Hours run 11 a.m. to 4 p.m. on Saturdays and Sundays, with the market closed Dec. 7.
5. Spend a seasonal afternoon at Christmas at Fairview Tree Farm.
Less than 10 minutes away in Shelton, Christmas at Fairview Tree Farm offers hayrides with Santa, a Christmas Shoppe and fresh-cut or cut-your-own trees from Nov. 28 through Dec. 21. Families often stop for cocoa or hot cider donuts before walking the fields or browsing the shop. For added fun, the farm also hosts its Night of Lights hayride beginning Nov. 29 on select evenings (advance reservations required).
6. Find holiday décor and gifts at Seven Maples Gift and Garden.
Seven Maples Gift and Garden, a Monroe gem, carries a mix of home décor, candles, accessories and items from both local artisans and national brands. The shop makes it easy to pick up hostess gifts, teacher presents or something to refresh your own decorating at home. During the winter season, the shop also stocks Christmas trees and wreaths for an extra dose of merry.
7. Catch a holiday performance at the Shubert Theatre.
Round out an evening in New Haven with a trip to the Shubert Theatre, where a lineup of seasonal productions fills the historic space each year. This season includes shows such as Miracle on 34th Street the Musical, The Nutcracker and Ireland with Michael – A Celtic Christmas. Dates and ticket details are listed on each event’s page for easy planning.
8. Ride a vintage trolley to visit Santa.
All aboard for holiday cheer! The Shore Line Trolley Museum in East Haven offers heated, decorated trolley rides to meet Santa, starting Thanksgiving weekend through Dec. 21. Children receive a small gift during their visit, and guests can enjoy hot chocolate before exploring the museum’s themed trolleys. Note: Because parts of the experience take place outdoors, warm layers are recommended.
9. Settle in for a cozy winter meal at Flames Restaurant.
After a long day of holiday errands, stop into Flames Restaurant on Main Street for hearty Italian dishes in a warm, comfortable setting. Standout entrées include Chicken Martini, Chicken Burrata and New York Strip Pizzaiola, with desserts and cocktails for a relaxed end to the evening. Locals and visitors alike rave about the generous portions and attentive service.
10. Visit a student-run bookstore at Next Chapter Books.
About 15 minutes from Monroe is a unique spot called Next Chapter Books, which serves as both a bookstore and a training space for students in Trumbull’s ELITE program. Visitors can browse a curated selection of books, order a warm drink or simply enjoy the welcoming atmosphere amidst the holiday hustle and bustle. As part of the ELITE program’s mission, the shop also gives students opportunities to build life and employment skills.
11. Slow down with afternoon tea at Posh Tea Room.
Sometimes, a good cup of tea is all you need to warm up and unwind. Monroe's own Posh Tea Room offers imported teas, seasonal scones and petite pastries, all served in an elegant setting with live piano music. Its thoughtful service and warm atmosphere make it a pleasant choice for small gatherings or peaceful solo visits. Guests can select from the full Afternoon Tea, the lighter Cream Tea or the single-guest “Elegant Exhale” experience. Reservations are recommended, especially on weekends.
12. Drive through the Fantasy of Lights display in New Haven.
A longstanding regional tradition, Fantasy of Lights at Lighthouse Point Park offers a drive-through shoreline route of illuminated winter scenes. The display runs Nov. 21 through Dec. 31, 5 to 9 p.m. Sunday through Thursday (extended hours until 10 p.m. on Fridays and Saturdays). Admission is $10 per car, $25 per minibus and $50 per full-size bus, with proceeds supporting Goodwill of Southern New England.
