A Local Guide from The Staci Zampa Team
The holidays in Stamford hit differently. The city feels festive and lively, but still carries that small-town warmth Staci always talks about. Whether you’re new here, moving from NYC, or a longtime local planning out your December, there’s no shortage of things to do. Stamford is packed with family-friendly holiday events, shopping markets, community gatherings, and signature traditions that bring everyone together.
Here’s your complete guide to the best holiday events happening in Stamford for 2025—curated by The Staci Zampa Team, your trusted local real estate experts and community partners.
Heights and Lights
December 7 | 5 PM | Downtown Stamford
Heights and Lights is Stamford’s most iconic annual holiday event. It’s the one that makes every local stop in their tracks—even if they’ve seen it a dozen times.
Picture this: Santa, Rudolph, and friends rappelling down the side of one of Stamford’s tallest buildings, followed by a full tree-lighting celebration and holiday music. Kids love it, adults love it, and if you're new to Stamford, this is the perfect introduction to the energy of the city.
Expect live entertainment, food vendors, photo ops, and a lively crowd. If you're planning to bring kids, arrive early to get a good spot near the main stage.
Best for: families, newcomers, holiday photos, festive night out
Pro tip: Parking fills up quickly; try to carpool or grab a rideshare if possible.
Holiday Wish Express at Stamford Town Center
Starts November 22 | Stamford Town Center
If you’re looking for a kid-friendly holiday experience that’s easy, accessible, and fun, the Holiday Wish Express at Stamford Town Center is the move. This immersive, themed experience takes children through a magical holiday “journey,” complete with festive décor, interactive moments, and plenty of surprises.
It’s designed to feel like a mini North Pole adventure indoors—perfect for colder days or last-minute activities before or after holiday shopping. It’s also conveniently located within the mall, so families can pair it with lunch, photos with Santa, and gift hunting.
Best for: young kids, parents, rainy day activities
Why locals love it: It’s convenient, affordable, and great for filling an afternoon.
Holiday Market Weekend at Mill River Park
Image Source: https://www.stamfordmuseum.org/holiday-market
December 6–7 | 10 AM–6 PM | Mill River Park
Mill River Park is one of Stamford’s most beloved community spaces, and their Holiday Market Weekend is becoming a local tradition. For two full days, the park transforms into a European-style outdoor holiday market with local vendors, handmade goods, seasonal treats, and festive music.
Expect a curated mix of artisans selling everything from candles and jewelry to baked goods and holiday décor—perfect for finding unique gifts you can’t get anywhere else.
Best for: holiday shopping, supporting local vendors, weekend plans
Tip: Bring a tote bag and some cash; a few vendors operate independently without card readers.
DBL Small Business Holiday Market
November 29 | 11 AM–3 PM | Downtown / DBL
If you’re passionate about supporting small businesses, this should be at the top of your list. The DBL Small Business Holiday Market is a pop-up shopping event highlighting Stamford’s local makers, creators, and entrepreneurs. It’s smaller and more intimate than the bigger markets, but that’s part of the charm.
You’ll find boutique gifts, seasonal treats, décor, and a warm, festive atmosphere that feels like a true community event. It's also a perfect way to kick off the holiday shopping season right after Thanksgiving.
Best for: unique gifts, small business supporters, holiday browsing
Bonus: Great way to discover new Stamford-based creators.
Crafted Wreaths & Cocktails at DBL
December 5 | 6 PM | DBL
If you want a holiday event that feels fun, creative, and a little elevated, Crafted Wreaths & Cocktails is the one. This workshop blends hands-on wreath making with seasonal cocktails for an evening that feels festive and social.
It’s perfect for a girls’ night, date night, or just breaking up the December rush with something relaxing and creative. Space is usually limited, so booking early is smart.
Best for: couples, friends, creative holiday experience
Why it’s special: You walk away with a custom wreath that looks professionally done.
Stamford Moms’ Third Place Vendor Event
Image source: https://stamfordmoms.com/the-stamford-moms-holiday-sip-shop/
December 7 | 10 AM–2 PM | The Third Place
Stamford Moms is known for curating great local events, and their Third Place Vendor Event is one of the best family-friendly holiday shopping experiences in town. You’ll find a mix of local vendors, kid-friendly activities, and community members gathering for a relaxed, festive day.
This event is especially popular among parents looking for thoughtful gifts, kids’ items, or a wholesome way to spend a December morning.
Best for: families, gift shopping, new residents looking to meet locals
Added bonus: It’s a great chance to connect with the Stamford Moms community.
Stamford SantaCon
Image Source: https://www.santacon.info/Stamford-CT/
December 6th | Meet at 12 noon on Bedford Street
Yes—Stamford has its own SantaCon, and it’s a staple for young professionals and groups of friends looking for a festive bar-crawl style holiday outing. Expect themed outfits, drink specials, holiday music, and a playful atmosphere across multiple downtown bars.
While it’s definitely a rowdier event, it’s also a fun way to tap into Stamford’s nightlife scene during the holiday season.
Best for: adults, bar crawls, holiday nightlife
Tip: Plan transportation ahead of time. Downtown gets busy quickly.
Why Stamford Shines During the Holidays
One of the reasons so many people are moving from NYC to Stamford is because the city offers the perfect balance—city energy with small-town heart. Holiday events here feel connected, genuine, and community-driven, and each neighborhood puts its own spin on the season.
Families love it because there’s always something to do. Young professionals love it because there’s nightlife, creative events, and local markets. And longtime residents get to enjoy traditions like Heights and Lights that bring the whole city together year after year.
Moving to Stamford? Let The Staci Zampa Team Guide You
Stamford isn’t just a place Staci sells real estate—it’s her hometown, and she’s spent over 30 years helping families, newcomers, and lifelong locals find their perfect place here.
If you’re relocating, exploring neighborhoods, or planning a move in 2025, Staci Zampa is here to help you navigate the market, learn the area, and feel right at home.
Explore more neighborhood guides and relocation resources at stacizampa.com
