Top 10 Holiday Events in Portland, Maine

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The holidays are a time for family, friends and traditions. Whether you are a Portland, Maine native or traveling to Portland for the holidays, our city has a ton of holiday events that have become classic ways to celebrate. 

From shopping to holiday decor, dining to themed events or fitness we’ve got something for you!

Our team has rounded up our top 10 holiday season favorites in and around Portland that are sure to bring you joy. So throw on a scarf and bundle up... it’s time for an adventure as we celebrate the holidays in Portland, Maine!

1. Monument Square Tree Lighting

A not to be missed annual event happening this year on November 29th from 4-6pm. 

The evening will feature live entertainment, a visit from Santa himself and the lighting of the giant tree right in the center of Monument Square. Learn more here.

*Insider tip: Reserve a table, or snag a barstool, at a nearby restaurant like David’s or Shay’s for a front row seat.


2. Christmas at the Victoria Mansion

During the holidays the event calendar at the Victoria Mansion lights up (in addition to the property itself of course) with unique festive experiences for visitors. 

The building itself transforms, both inside and out, with each room inside decorated by a different designer and the exterior expertly sprinkled with garland and lights.

Whether you are looking for something family friendly, a fancy night out at a gala or something for the art lover in your life the Victoria Mansion has something for you. Check out their full list of events here.


3. Get Outside & Get Active

Even though it’s chilly you can still enjoy the outdoors and burn off some of those holiday calories. Two of our favorite festive fitness activities are The Portland Trails Holiday Dash and The Santa Hustle which are both 5k races designed for all levels of runners and great for the entire family.


4. Holiday Happy Hour

The holiday season is a great time to get together with friends, family and coworkers alike...and what better place to do so than at Happy Hour?! 

You can stick to our local Happy Hour favorites like Scales, Chaval, Inkwell at the Press Hotel, SurLie (and more) - or you can go a bit more official and check out the Wonderful, Magical, Fantastical Holiday Happy Hour. Hosted by Maine Spirits this happy hour event features an evening of cocktail samplings, hors d’oeuvres and fine adult spirits.

*Insider tip: Take advantage of $5 off an Uber to and from the event with your ticket purchase.


5. Merry Madness

Do you enjoy shopping, holiday deals, supporting local businesses and tasty beverages? 

Then this one's for you!

This year’s Merry Madness shopping extravaganza will be held on Thursday, December 5th from 4-10pm. The evening will include shopping at a long list of participating local businesses who extend special holiday offers and a refill of your ‘merry’ cup as you go. It’s a great event to attend with a group - and even more fun with matching holiday outfits! Learn more & snag your tickets here.


6. Alllll Aboard….The Polar Express

We might not have Tom Hanks here in Portland (although you never know…) but we do have The Polar Express!

This holiday experience is the largest event hosted the Maine Narrow Gauge Railroad Co. & Museum and draws over 19,000 visitors from near and far each year (so, hint, hint... get your tickets in advance).

The train cars are fully outfitted with holiday decor so that you’ll feel like you are right on the movie (or book) set - plus you can enjoy hot chocolate, cookies and a live reading of the classic tale as you travel to the “North Pole.”

Best part? Santa greets you upon your arrival and you can join in on sing-along carols while aboard.


7. Portland Harbor Parade of Lights

This annual event is unique to our city offering a magical waterfront experience that lights up the entire Casco Bay harbor. Local boat owners and fisherman decorated their vessels in festive Christmas lights and parade through the harbor topped off with an impressive fireworks display at the conclusion of the parade. Learn more here.

*Insider Tips: Get tickets on the Casco Bay Cruise lines and watch the festivities from the water, reserve a table at a nearby restaurant on the water OR bundle up and secure a spot on the end of one of our fishing piers.


8. Enjoy a Show

Our very own Portland Symphony Orchestra offers a long list of holiday events including the classic tale of Peter & the Wolf  and the local fan favorite - The Magic of Christmas.

Insider tip: Snag a spot at the bar at Union over at the Press Hotel for an appetizer and cocktail before or after the show

If ballet is more your speed, be sure to check out ‘The Victorian Nutcracker’ with performances by the Portland Ballet and the Portland Ballet Orchestra with shows in both Portland and Westbrook. For more information and tickets click here.


9. Santacon

If you love Christmas, getting dressed up and a good holiday cocktail then you do not want miss Santacon. Held on December 7th starting at 4pm...and going into the wee hours of the morning, this is most definitely an experience. 

In it’s 12th year, you can join hundreds of other holiday goers dressed up as Santas, elves, reindeer, Christmas trees, snowmen and more for a bar crawl through the city stopping at all the Old Port’s most popular watering holes.


10. Visit The Rink at Thompson’s Point

Although this isn’t a dedicated “holiday” event, it’s something that you won’t want to miss during the winter season. Offering two outdoor ice skating rinks and multiple warming stations, including a winterized yurt with local food vendors, hot chocolate and alcoholic beverages for the adults, it’s definitely an #instagramworthy activity. Perfect for families, groups and a creative idea to spice up your date night during the holiday season.


No matter what you choose, you are in for a treat this holiday season in Portland. We love our city all year round, but there certainly is something magical about our seaside city during the holidays. 

We’d love to hear some of your holiday favorites in the comments!