Hear those sleigh bells ring? Jingling, ring tingle tingling too? Then it must mean the holidays are finally here and we can’t think of a more magical and festive place to celebrate the spirit of the holidays than in Portland, Maine! And while Santa puts the finishing touches on his lists, we have rounded up our personal list to spending the holidays in Portland, including shows, events, dining experiences and more! Check it out.
Visit the Monument Square Tree
No holiday season in Portland is absolute until you visit Portland’s signature Christmas tree. Lighting up Monument Square every year, you can enjoy the beauty of this year’s tree in-person day or night, as well as, virtually through Portland Downtown’s TREECAM. Illuminated against the backdrop of Monument Square and Our Lady of Victories Monument, this 50-foot Balsam Fir originates from 35 Lubec St. in South Portland.
Can’t get enough of the Christmas trees? Head on down to the Old Port and visit Portland Regency and Spa’s lobster trap tree or keep going until you hit Portland’s waterfront where you will spot Luke’s Lobster’s own take along Portland Pier. Getting in on the holiday cheer, new this year, The Porthole additionally has a lobster trap tree for holiday enthusiast can check out! Paying homage to the lobsterman and woman roots of Maine, these lobster trap trees are equally as fun in the day as when illuminated at night.
Shop ‘Til You Drop in the Heart of the Old Port
It is the season of giving after all! The Old Port is known for its local shops and boutiques, and thus makes it the perfect place to cross those names off your Christmas list. All within walking distance from each other, here are few suggestions to push you in the right direction.
For the individual who just can’t get enough of the Pine Tree State, head on over to The Maine Souvenir Shop, a locally motivated shop built on the promotion of Maine. Ideal for local Maine gifts, treats, art, and clothing.
If you’re searching for the fashionista in your life, look no further than Bella Funk on Exchange St., which is a boutique that offers women’s clothing and more for the creative lifestyle.
For the cool kid? Mocean Skateboards on Exchange St. offers everything from skateboards to vintage vinyl and apparel featuring art from local artists. For your cannabis-loving friend? Stop on into Jar Cannabis or Fire on Fore for the latest and greatest in the growing world of cannabis. And don’t forget a gift for the lover of all things handmade and costumed designed! CHART Metalworks sells beautiful women and men’s jewelry and accessories, barware, and home goods inspired by the rocky coast of Maine.
Shopping for the family? Does dad need a new book? Make a stopover at Sherman’s Bookstore on Exchange Street, while mom might enjoy the one-of-a-kind custom-made jewelry from Designs By CC or D. Cole Jewelers, a family-owned shop specializes in handcrafted platinum, gold, and sterling silver jewelry pieces. A gift for your beloved family pet? Choose from a range of fun and festive toys, treats, leashes, collars, and more from the most adorable mom-and-pop pet shop, Uncommon Paws.
Looking to hit your list all at once? Saturday, December 16th, 2023 from 12pm – 5pm, Fete Market is teaming up with Toad & Co., a clothing store creating their own line of eco-friendly clothing for men and women, to bring to Portland the Sustainability Holiday Fete Market. An indoor holiday market that will highlight sustainable makers, Fete Market features a laid back, family vibe, where shoppers can enjoy live music from Night Hawk Band, local food, and Maine brews as you shop the work of 20+ local artists and creatives.
On Sunday, December 3rd and 17th, 2023 from 10 AM – 3 PM join Thompson’s Point as they host Maker’s Market for another year. Featuring an extensive list of local artists, makers, farmers, craftspeople, and more, the best part about Maker’s Market (aside from supporting local) is the fabulous mimosas and Bloody Marys available for purchase as you shop.
Over at Indigo Arts Alliance we see the return of their Holiday Pop-Up Shop, an opportunity to take home exquisite works of art from their past Artists-In-Residence and some of the incredible Black and Brown artists in the global community. Happening Thursday, November 30th – Sunday, December 3rd and again Thursday, December 7th – Sunday, December 10th, 2023 from 12pm-7pm at their studio at 60 Cove Street.
Plan a Tour at Victoria Mansion
Christmas at Victoria Mansion (a house museum with original Herter interiors from the 1860s) is a can’t miss event. The result of local and up-and-coming florists, designers, artists, and fellow non-profits organizations coming together to utilize the backdrop of the Mansion’s interior design to create unique decorations that emulate Victorian-era splendor. Now in its fourth decade, Christmas at Victoria Mansion welcomes thousands of visitors each year from the end of November through the beginning of January.
Tours are self-guided and offered Tuesdays through Sundays 10 AM – 4 PM with the last admission at 3 PM. Tickets are now available and it’s recommended that you purchase tickets online in advance here.
Hop on the Polar Express
This year’s fun begins at Portland’s Ocean Gateway Marine Terminal, where the Conductor will board passengers onto the 9 historic coaches decked out for the holidays. Once aboard, Christmas music will fill the cars as the steam locomotive, powered by beloved Steam Engine #3, thunders to the “North Pole”. Children will see Santa waving to all aboard the train as he prepares his sleigh for departure. Hot chocolate and cookies will be served onboard by the magical chefs.
Coach seating and first-class tickets are available online. First-class tickets get you seats in the beautifully restored historic railroad cars and will received limited-edition ceramic mug as a unique souvenir of their train ride to the North Pole.
Train times run at 1:30 PM, 2:45 PM, 4:00 PM, 5:15 PM, 6:30 PM, AND 7:45 PM on select dates between Friday, November 24th – Saturday, December 23rd.
Enjoy the Magic of Christmas
Now in its 44th year, watch this beloved holiday tradition in-person at Merrill Auditorium. A family-friendly performance presented by the Portland Symphony Orchestra, this year’s show will be led by Music Director Eckart Preu. You can celebrate the season with Christmas classics new and old – including the beloved “Sleigh Ride!” and “A Holly Jolly Christmas” by purchasing your tickets today online!
View the Portland Parade of Lights Along the Waterfront
The City of Portland invites you to join in on the Parade of Lights of Portland’s favorite tugboats, lobster boats, and ferry boats! Happening December 16th, 2023 at 4:30 pm, the Parade of Lights takes place out on Casco Bay but spectators can take in the lights display at plenty of waterfront spots including the Maine State Pier, Luke’s Lobster Portland Pier, and Bug Light Park in South Portland.
Dine Your Heart Out
Dine your heart out in this foodie city! During this time of year, local restaurants put on their holiday best and deck their own halls with festive wreaths, garlands, lights, poinsettias, trees, holiday cocktails and specials.
Starting soon, you can head on over to Blyth & Burrows for their own take on a holiday movie classic, A Christmas Story, with their “Fra-Gee-Lay” cocktail made with Roasted Chestnut Bourbon, Creme de Cacao, Cynar, Mole Bitters, Egg…”It must be Italian!”
*November 28th, 2023 Update: cocktail is not on the menu yet but will return for the holidays soon!
To dine in the classiest of holiday decor, head to ViA VECCHiA a small plates Italian restaurant in the Old Port. Beautifully draping floral arrangements of poinsettias, roses and more across the dining room, the holiday spirit is only enhanced with ViA VECCHiA’s holiday cocktail menu now available.
Making Santa’s Nice List, Hunt and Alpine, a renowned cocktail bar in Portland’s Old Port, has dressed up their space for the holiday season! Introducing their Reindeer Bar, now open through Sunday, December 31st, Hunt and Alpine is offering an adult take on a childhood classic, boozy hot cocoa. The festive fun doesn’t stop there. The holiday bar is also offering Egg Nog and Spanish Coffees for the occasion.
Over in the West Bayside area, Batson River Brewing & Distilling is once again going above and beyond with their “Holiday Camp.” Becoming THE holiday destination (and the perfect place for a holiday selfie or group shot to share on your socials), upon arrival, you are greeted with festive cheer in the form of extravagant Christmas trees, Christmas lights, holiday cocktails, wreaths, presents and more!
Attend Holiday Shows!
With the holiday spirit high in town, the list of events and holiday shows is quite long! Mark your calendars for the following shows:
- A Christmas Carol with Portland Stage Co. Saturday, December 2nd – Sunday, December 24th, 2023.
- Rock My Soul at One Longfellow Square on Sunday, December 17th, 2023. An evening of R&B, pop, soul, and doo-wop flavored arrangements of Christmas carols and popular holiday favorites.
The Fogcutters Superfantastic Christmas Extravaganza! at State Theatre on Saturday, December 16th, 2023.
- Keelan Donovan: Home for the Holidays at The Portland House of Music on Thursday, December 14th, 2023.
- The Chad Banks Christmas Special at Citrus
- and Vivid Motion Dance Presents: ‘Twas The Night Before… Burlesque at The Hill Arts, Friday, December 8th – Sunday, December 10th, and Wednesday, December 13th – Saturday, December 16th.
For the full list of holiday happenings head to our Events Calendar here!