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, which is on around the clock. Illuminated against the backdrop of Monument Square and Our Lady of Victories Monument, this 40-foot Balsam Fir originates from Anne and Toby Nappi’s yard in the neighboring town of Westbrook, Maine where it was planted 23 years ago as a lovely addition to the yard with no indication of just how large the tree would become and the future it would hold.
Can’t get enough of the Christmas trees? Hop on down to the Old Port and visit Portland Regency and Spa’s Lobster Trap Tree or keep going until you hit the Portland Pier waterfront where you will spot Luke’s Lobster’s own take (As of November 28th, 2022 Luke’s Lobster tree is currently under construction and will be up soon). 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, the following are a 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, then look no further than Bobbles & Lace on Milk Street, which offers high fashion at affordable prices. For the cool kid? Mocean Skateboards on Exchange Street offers everything from skateboards to vintage vinyl and apparel featuring art from local artists. Don’t forget the planner in your life! Gus and Ruby Letterpress offers a selection of curated gifts and paper goods from notebooks, planners, candles, and more.
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.
Looking to hit your list all at once? Happening December 2nd from 2pm-7pm, 3rd and 4th from 12pm-4pm, Needfire Candle Co. in the Old Port is hosting a Winter Faerie Market with ornaments, cards, rings, jewelry, stickers, art and more from local vendors.
On Sunday, December 4th and 18th from 10 AM – 3 PM join Thompson’s Point as they host Maker’s Market for another year. Featuring with 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 December 1st – 4th, 2022 from 12pm-8pm at their studio at 60 Cove Street, this year expect an ethereal Sunday Soundscape from DJ Kafari to close out the final day of the shop Sunday from 2 PM – 4 PM.
For more holiday gift ideas and where to shop head to our Portland, Maine Gift Guide here.
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 has in the past welcomed over 8,000 visitors each holiday season.
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
All aboard the Polar Express at the Maine Narrow Gauge Railroad Co. & Museum! Drawing over 20,000 passengers in 2021, this rolling history museum has become a holiday tradition for families alike. 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 onboard, 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 here. 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 2:45 PM, 4:00 PM, 5:15 PM, 6:30 PM, AND 7:45 PM on select dates between November 25th – December 23rd.
Skate at The Rink at Thompson’s Point
2022 – 2023 Update: CLOSED for renovations but keep at the top of your list for next holiday season! See more here.
Returning for another season at Thompson’s Point, The Rink will be open again soon the next holiday season. Located outdoors and offering sunset views across Fore River, enjoy your skating experience with up to 10,000 sq. ft. of ice surface.
Hungry? The Snack Bar offers hot dogs and pretzels. Getting cold? For the kiddos, hot cocoa is available upon purchase while heated areas will also be provided including the yurt bar offering local beers on tap, wine, and hot cider. Special events and themed nights to come!
Enjoy the Magic of Christmas
Now in its 43rd 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 Saturday, December 17th at 4:30 PM out on Casco Bay, spectators can take in the lights display at plenty of waterfront spots including DiMillo’s and the Maine State Pier.
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, 2022 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 the Naughty List, Après, a craft seltzer and cider house in Portland’s East Bayside, has also dressed up their drink list for the winter with an adult take on a childhood favorite – boozy hot cider! Getting creative with their specials, find exampled above their limited hot + boozy cider special from late November. Made from local pressed apples, soft brandy, topped with anise and maple cotton candy our insider intel can tell you that this one time popular special may just return again soon so keep an ear to the ground! Until then get cozy and merry at Après with their boozy hot cider and festive smörgåsbord of holiday decor.
Over in the West Bayside area, Batson River Brewing & Distilling has gone above and beyond and has become a holiday destination for their “Holiday Camp.” Upon arrival, you are greeted with festive cheer in the form of extravagant Christmas trees, Christmas lights, holiday cocktails, and a tinseled “Tomfoolery” backdrop, perfect for that holiday selfie or group shot to share on your socials.
Attend Holiday Shows!
With the holiday spirit high in town, the list of events and holiday shows is long! Mark your calendars for A Tuna Christmas with Portland Stage Co. now until December 24th, 2022, a Charlie Brown *Jazz* Christmas at One Longfellow Square on December 4th, a Drag Holiday Brunch show at Luna Rooftop Bar on December 11th, and a Super-fantastic Xmas Extravaganza with The Fogcutters at The Portland House of Music on the 17th, and a Don Campbell Christmas at St. Lawrence Arts on December 21st.
For the full list of holiday happenings head to our Events Calendar here!