Seasonal & Holidays
12 Days Of Cheer In New Haven: 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 New Haven. 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 New Haven 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. Shop local at the magical Winterfair inside New Haven Union Station.
Winterfair brings more than 30 local vendors to the second level of Union Station’s Great Hall every Saturday and Sunday from November 29 through December 21. The market rotates over 100 small and diverse businesses throughout the season, giving you something new to browse each weekend, from handmade gifts and artwork to specialty foods and holiday décor. Hours run from 11:00 a.m.–4:00 p.m., and the lively setup makes it easy to stroll the stalls with family or pick up unique presents as part of a day in the city.
Find out what's happening in New Havenfor free with the latest updates from Patch.
2. Ride the historic trolley and visit Santa at the Shore Line Trolley Museum.
The Shore Line Trolley Museum hosts a festive trolley ride where families can meet Santa, enjoy cocoa and explore holiday-decorated trolleys throughout the grounds. The event runs Thanksgiving weekend and weekends in December through December 21, with heated trolleys that make the ride comfortable even on colder days. Kids can share their wish lists, receive a small gift and take photos, and the museum’s exhibits remain open for browsing after your ride. Much of the experience takes place outdoors, so dress warmly to enjoy everything the museum has set up for the season.
3. Hit the ice at SKATE New Haven.
SKATE New Haven welcomes skaters to the Ralph Walker Skating Rink, offering open skate sessions throughout the season with admission at $10, $8 for New Haven locals and $7 for skate rentals. Schedules vary week to week, and the rink posts all open skate times, last-minute changes and weather updates on Facebook and Instagram. Group classes, stick times and other programs return for the 2025–2026 season, and residents must show proof of address for discounted admission. Check the rink’s latest posts before heading out so you know exactly when the ice is open.
Find out what's happening in New Havenfor free with the latest updates from Patch.
4. Drive through the glowing displays at Fantasy of Lights.
A 30-minute drive brings you to Lighthouse Point Park, where Fantasy of Lights fills the shoreline with illuminated scenes that have become a long-running tradition for families across southern Connecticut. Colorful arches, animated figures and themed installations line the route, offering a bright, festive way to enjoy a December evening from the warmth of your car. The display runs through December 31, with Sunday–Thursday hours from 5:00–9:00 p.m. and extended hours until 10:00 p.m. on Fridays and Saturdays. Admission is $10.00 per car or family van, with higher rates for minibuses and full-size buses, and ticket proceeds support Goodwill of Southern New England.
5. Find warmth and community at MOTW Coffee and Pastries.
When you need a moment to breathe during the holiday rush, MOTW Coffee and Pastries is the kind of place that instantly makes you feel at ease. The café grew out of the global “Muslims of the World” community, and that spirit of storytelling and kindness comes through in both the people and the space itself. You can grab a seasonal latte to take to go, bring your family in for a treat or sit for a few minutes before heading to your next stop. With its range of traditional coffees, espresso drinks and fresh pastry options, it’s a warm spot that feels especially comforting during the winter season.
6. Browse thoughtful gifts and home goods at Dwell New Haven.
Stepping into Dwell New Haven feels a little like visiting a beautifully curated home, with shelves filled with textiles, apothecary items, jewelry, baby gifts and pieces sourced from makers near and far. The shop sits in the Historic Chapel Street District, making it a great stop while you’re exploring the area’s theaters, restaurants or Yale’s campus during the holiday season. You’ll find everything from rich linens and cozy sleepwear to aromatic candles and artisan-made décor, all hand-selected by the owner to create a warm, welcoming mix of textures and styles. Stop by to pick up thoughtful gifts or browse with your family as you add a few seasonal touches to your own home.
7. Catch a live holiday performance at the Shubert Theatre.
The Shubert Theatre brings Broadway-style magic to downtown New Haven, especially during the holidays when its stage fills with seasonal productions for all ages. The historic venue opened in 1914 and still carries that classic theater charm, making shows feel intimate and immersive from the moment you take your seat. This year’s lineup includes favorites like Miracle on 34th Street the Musical, The Nutcracker and Ireland with Michael – A Celtic Christmas, along with other festive performances throughout December. Check the theater’s event calendar in advance to view upcoming shows and reserve your tickets.
8. Enjoy a cozy dinner at Cast Iron Chef Chop House & Oyster Bar.
Cast Iron Chef Chop House & Oyster Bar delivers a warm, easygoing atmosphere to downtown New Haven, serving expertly prepared steaks, seafood and daily specials. The restaurant is known for its cast-iron skillet cooking, a technique the chef has honed for more than a decade to create perfectly seared, deeply flavorful dishes. You’ll find Prime Angus beef hand-cut on site, along with lamb, duck and fresh seafood options that work well for a winter night out. It’s a comfortable place to settle in with family or friends, especially if you’re looking for a festive meal to pair with your holiday plans.
9. See the lights along the Reindeer Route in nearby Branford.
About 15 minutes from New Haven, Branford’s Reindeer Route invites families to drive through town and enjoy homes and businesses decked out for the season. Participants decorate their spaces with creative, colorful and holiday-themed displays, and the town awards prizes for categories like Most Creative, Holiday Spirit and Most Colorful. The official map becomes available online by December 10 and begins at the Town Green, where the Holiday Tree and Menorah set the tone for the route. Plan your route once the map is posted so you don’t miss any of the standout displays.
10. Gather for a winter pint at East Rock Brewing Company.
The family-owned East Rock Brewing Company brings a community-focused feel to the historic neighborhood it’s named for, offering crisp German-style beers made with time-honored brewing methods. The beer hall pours 12 drafts alongside specialty releases, locally sourced cocktails, cider and wine, making it a comfortable spot to meet friends during the holiday season. Seasonal events often fill the calendar this time of year, including Winter Tour & Pour nights, holiday movie trivia and a festive winter market. Visit East Rock’s event page to see what’s coming up during your visit.
