A Coastal Holiday: How Maine Celebrates the Season + Where to Shop
The winter season in Maine is its own kind of beautiful. While the days are short and the temps are cold, once the sun sets and the lights come on, something shifts. Every town from Portland to the midcoast starts to glow with that coastal holiday charm, just a little quieter, a little quirkier, and yes, a little saltier than elsewhere.
Whether you live here or you’re planning a trip to find out if Maine is right for you and your family, now is the time to explore Maine in a way many never do, under twinkling lights, near a bustling brewery fire pit, or elbow-deep in a Maker’s Market, discovering gifts that were designed right here. Bundle up, warm your heart (and your hands), and let’s make this season one to remember.
Magic Awaits at Gardens Aglow
November 15 – January 3 | Coastal Maine Botanical Gardens (Boothbay)
If you’ve never seen a garden glow, you’re in for something unforgettable. Each winter, the Coastal Maine Botanical Gardens transform into a world of light, featuring more than half a million bulbs woven among towering trees, sculptural installations, winding paths, and coastal woodland.
Gardens Aglow is a beautiful space to wander with the people you enjoy most. You can take your time, follow the trails, and experience the gardens in a completely different way than you would in summer. It’s an annual tradition for many Mainers, and once you’ve seen it for yourself, it’s easy to understand why.
Imagine By Coastal Maine Botanical Gardens
Monument Square Tree Lighting
November 28, 2025 | Downtown Portland
Portland’s holiday season officially begins in Monument Square, where the annual Tree Lighting event draws families, friends, and neighbors for an evening filled with simple tradition and plenty of energy. Festivities begin at 4 PM, with free hot cocoa, holiday photo booths, live entertainment, and a few extra surprises, like a Buddy the Elf look-alike contest and a free outdoor screening of Elf to keep the crowd entertained.
The main event happens at 6:30 PM, when a 50-foot tree is illuminated with thousands of LED lights, right in the heart of downtown Portland. It’s followed by the lighting of Pandora’s Winter Lights across the city, turning streets, storefronts, and alleyways into a glowing reminder that winter has truly begun in Maine. This is one of Portland’s most iconic holiday traditions, and every year it delivers the same mix of community spirit and seasonal excitement.
Image By: Portland Downtown
Holidays on the Rocks: Rock Row’s Makers Market + More
November 30 – December 31 | Westbrook
Rock Row in Westbrook has turned winter into a full-on experience with its month-long “Holidays on the Rocks” celebration. The heart of it is the Makers Market, held Thursday through Saturday, featuring a curated group of Maine artisans and creators. From hand-poured candles and small-batch body care products to original artwork and custom wood pieces, it's a thoughtful and refreshing alternative to big-box holiday shopping. It's a chance to meet the makers and find something with personality, something that feels like Maine.
Sundays bring a different kind of gathering around the fire pits. Lone Pine Brewing offers take-home s’mores kits, and families and friends settle in around the flames with something warm in hand. It’s simple, relaxed, and a reminder that winter can be about lingering, not rushing. Plus, on the weekends, you’ll find live ice sculpting on site. Local artists shape blocks of ice into coastal-themed sculptures right in front of the crowd, adding a bit of wonder to the weekend lineup. Whether you're shopping, sipping, or just soaking in the atmosphere, Rock Row has turned what can be a quiet stretch of winter into a season of connection and creativity.
Image By: Rock Row
Freeport’s Sparkle Celebration
December 5 (Parade) + December 14 | Freeport
Freeport knows how to put on a holiday celebration, and its annual Sparkle Celebration brings together everything you love about a coastal Maine town in winter. On Friday, December 5, the Sparkle Parade of Lights makes its way through town, leading up to the moment when Freeport's well-known Talking Tree is lit for the season, a long-standing local tradition.
The festivities continue on Saturday, December 14, with a full day of outdoor fun. Expect crackling bonfires, live music, food trucks serving local favorites, and an impressive lineup of Maine artisans offering a diverse range of handmade goods, including pottery, paintings, and more.
Image By: Visit Freeport
Winter Classics: Lace Up Those Skates at Thompson’s Point
Opens November 28 | Portland
There’s something special about ice skating outdoors in Maine, and Thompson’s Point has turned it into a tradition. The rink is back this season, along with all the familiar extras that make it more than just a place to skate. You’ll find a beer garden pouring local brews, fire pits ready for warming up in between laps, and tucked-away VIP corners if you're looking for a quieter spot to gather.
Whether you're lacing up skates yourself or watching the kids loop around under the lights, this rink has a way of making winter feel active and joyful. It’s casual, lively, and one of the easiest ways to get outside and feel connected to the season, and to Portland.
Image By: Thompson’s Point Rink
Portland’s Merry Madness + Shopping Local
November 28 – December 13 | Downtown Portland
If your holiday shopping routine has turned into a blur of online carts and generic gifts, Merry Madness is your chance to turn things around, Portland-style. This two-week shopping crawl lets you ditch the rush and wander at your own pace, hopping between downtown boutiques and makers’ shops. As you collect stickers from each stop, you’re not just meeting your gift list, you’re entering to win local prizes and discovering the charm behind each small business.
Whether you’re in it to win the prize or simply to enjoy the side streets and shop windows on a quiet December afternoon, Merry Madness reminds you what holiday shopping can feel like: local, personal, and, somehow, just right.
Image by: Portland Downtown
Wrapping Up the Season
In Maine, the holidays are shaped by simplicity, tradition, and community. Whether you’re visiting for a long weekend or already live along the coast, winter has a way of reminding you what matters most: good people, good places, and a slower pace. And no matter how well you know the area, there’s always something new to discover, especially this time of year.
If you’ve ever thought about making Maine your home beyond the holidays, I’d be happy to help you explore what coastal living here could look like in every season.
