Seasonal & Holidays
12 Days Of Cheer In Woodbury: 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 Woodbury. 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 Woodbury 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. Support the Winter Lights of Woodbury.
Walk around town and soak in the holiday magic while looking at the Winter Lights of Woodbury. A community tradition, volunteers decorate trees throughout the town with orbs to create a festive atmosphere. The group also raises money for charitable causes through sales of raffle tickets, merchandise and seasonal lagers at local markets around town. Learn more about it on their Facebook page.
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2. Warm up with a cozy breakfast at West Egg Cafe.
Nestled in the heart of Woodbury, West Egg Cafe is the kind of spot locals love for a slow December morning. The cafe is known for its housemade baked goods, fresh breakfast plates and a warm, lived-in charm that makes it easy to linger. Whether you’re grabbing a latte before holiday errands or settling in for brunch with friends, the menu delivers comfort without feeling heavy.
3. Pick out your holiday greenery at Maple Bank Farm.
In winter, Maple Bank Farm in Roxbury transforms into a winter wonderland filled with handmade wreaths, bright red poinsettias and all the trimmings needed to bring the season home. Families return year after year to choose from a wide selection of precut and potted Christmas trees, each one arranged with care across the historic property. The farm is open Tuesday through Sunday, 10:00 AM to 5:30 PM.
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4. Tune in and watch the synchronized Elk Lights show in nearby Southbury
A short drive from Woodbury, Elk Lights brings more than 7,000 synchronized lights to life in a festive, music-driven display. Simply park, tune in to 92.9 FM and watch the lights dance along to curated songs that change throughout the season. The show runs nightly from 5:00 to 10:00 PM Sunday through Thursday and until 10:30 PM on weekends, though weather may affect hours. For updates and last-minute changes, check the Elk Lights Facebook page before you head over.
5. Browse one of Connecticut’s most charming bookstores at The Hickory Stick Bookshop.
Located in nearby Washington Depot, The Hickory Stick Bookshop has been a beloved literary hub for more than 70 years. With knowledgeable staff and shelves filled with books for every age, it’s the kind of place that makes holiday browsing feel like an event of its own. Beyond books, the shop carries puzzles, toys, journals, handcrafted gifts and even hickory walking sticks for winter hikes. Gilmore Girls fans will especially love the nods to Stars Hollow, making it a festive stop for both readers and nostalgia seekers.
6. Catch live music and seasonal brews at Woodbury Brewing Company.
Woodbury Brewing Company pairs house-brewed ales and lagers with a lively calendar of performances, making it a great local spot for a winter night out. With 16 beers on tap, weekly fresh batches and a full food menu, the brewery offers something for every taste, whether you lean toward stouts or sours. The family-friendly atmosphere includes shuffleboard, cornhole and plenty of space to unwind.
7. Shop local gifts at Newbury Place.
Set inside a 170-year-old vintage mill, Newbury Place is a go-to boutique for holiday gifts, seasonal accessories and curated finds from well-loved brands. The shop is packed with jewelry, clothing, home goods and specialty items, all wrapped with complimentary gift packaging that makes December errands a little easier. With a strong commitment to community support and philanthropy, the store has become a fixture for shoppers across Connecticut and beyond.
8. Glide across the ice at Danbury Ice Arena.
A short drive from Woodbury, Danbury Ice Arena offers public skate sessions on twin NHL-size rinks, making it an easy winter outing for families or friends. The arena features a full bar, café, arcade and skilled coaches on staff, so the experience is welcoming for beginners and seasoned skaters alike. Friday nights bring the high-energy DJ Skate event, complete with lights, music and a party-like atmosphere through mid-April. Check the public skating schedule before heading out. Rental skates are available.
9. Catch the hilarious holiday show ‘What the Dickens?’ at TheatreWorks New Milford.
Running December 5 through December 21, TheatreWorks New Milford brings back the crowd-favorite comedy What the Dickens? for another season of fast-paced fun. This playful twist on A Christmas Carol follows a troupe of actors trying to recreate the classic story entirely from memory, with plenty of mishaps along the way. The show blends Monty Python-style humor with holiday nostalgia for a performance that appeals even to self-proclaimed Scrooges. For performance dates and special events like pay-what-you-want night, see the event’s ticketing page.
10. Spend a sparkling evening at the Holiday Lights at Lake Compounce.
Just 35 minutes from Woodbury, the Holiday Lights Festival at Lake Compounce transforms the theme park into a glowing landscape of rides, treats and more than half a million lights. Kids can meet Santa, explore the holiday displays and see Connecticut’s tallest Christmas tree, while adults enjoy seasonal foods and relaxed nighttime rides. One-day tickets start at $19.99, with the option to purchase a 2026 season pass for free admission to this event. If you haven’t been before, this your last chance to visit: 2025 is the final year of the event, making it a must-do for families this season.
11. Explore handcrafted gifts at Brookfield Craft Center’s 50th Annual Holiday Shopping Tradition.
Celebrating its 50th year, the Brookfield Craft Center hosts a landmark holiday exhibition featuring works from more than 150 artists across ceramics, fiber, jewelry, wood, steel, and glass. The event runs through December 22 with extended shopping hours, making it easy to stop by even during busy weeks. Every purchase directly supports both the center’s educational programs and the independent creators behind the work. Whether you visit during Sip and Shop Nights or a weekend browse, the experience feels both festive and meaningful.
12. Experience the immersive holiday light displays at Glow Hartford.
About 45 minutes from Woodbury, Glow Hartford brings a million twinkling lights, interactive gardens and family-friendly attractions to the Connecticut Convention Center from Nov. 21 through Dec. 23. Visitors can explore illuminated tunnels, shop the holiday market, enjoy seasonal food and drinks and hop aboard the trackless “Glow-comotive” train. Kids will love Santa’s Sleigh Adventure, a playful scavenger hunt that winds through larger-than-life displays of trains, planes and cars. New this year is GlowQuest, an interactive wand-based experience included with every ticket, making the festival even more engaging for all ages. Purchase tickets online.
