What to do in Portland Maine

Celebrate the Holidays in Coastal Portland, Maine with a Week of Festive Fun


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Welcome to the beautiful seaside city of Portland, Maine, where a week of festive fun and cultural adventures awaits you! With its charming cobblestone streets and vibrant arts scene, Portland is packed with exciting events to round off 2024 with cheer.

Today, December 16th, kicks off with the annual Holiday Window Walk in the Old Port district. Stroll down Commercial Street and enjoy the spectacular holiday window displays created by local businesses. These artistic windows transform the historic streets into a glittering wonderland and offer a delightful way to get into the holiday spirit while supporting local shops. Most stores open their doors around 10 AM, making it a perfect start to your day.

As the week progresses, don’t miss the Portland Symphony Orchestra’s Magic of Christmas Concerts at the Merrill Auditorium from December 18th to 21st. Conducted by the charismatic Eckart Preu, this beloved tradition features timeless classics and contemporary holiday hits, all beautifully wrapped in orchestral brilliance. Evening performances start at 7 PM with matinee shows at 2 PM, so you have multiple chances to enjoy this delightful musical journey.

Art enthusiasts should mark their calendars for the First Light: Annual Holiday Exhibition at the Portland Museum of Art. On display until December 31st, this exhibit showcases extraordinary pieces by regional artists, many of which are available for purchase as unique holiday gifts. With the museum open from 10 AM to 6 PM, it's a perfect cultural respite from the winter chill.

For those looking to enjoy some New England festive dining, head over to DiMillo’s On the Water, the much-loved floating restaurant offering special holiday-themed menus throughout the week. Sink into the cozy cabin-like atmosphere with stunning views of Casco Bay while indulging in seasonal delights featuring fresh local seafood.

On December 21st, celebrate the Winter Solstice with Maine Audubon’s Solstice by the Sea at Gilsland Farm in nearby Falmouth. This family-friendly event runs from 5 PM to 8 PM and features guided lantern walks, storytelling, and warm beverages around a cozy campfire—perfect for embracing Maine’s natural beauty under the longest night sky.

To round off the week, enjoy some laughter at the Portland Comedy Connection’s Holiday HaHa Show on the weekend, showcasing the best local comedians on December 22nd and 23rd. Shows begin each night at 8 PM, promising doses of holiday humor to fill you with laughter and joy.

For a magical experience this weekend, immerse yourself in the Victoria Mansion’s Christmas tour. This opulent historic home is decked out in stunning period holiday decor. Self-guided tours are available from 10 AM to 3 PM, offering a unique glimpse into 19th-century celebrations with a touch of grandeur.

Portland, Maine, truly shines this week, offering something for everyone—from symphonic sounds and artistic delights to outdoor wonders and culinary treats. Bundle up, embrace the festive spirit, and make the most of your time in this charming city by the sea!
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