3 Festive Activities to Do in Portland, Maine This Holiday Season

Hannah Truman
Dec 1, 2023
2 min read

Updated: Sep 2

'Tis the season!

From admiring twinkling Christmas tree lights to twirling on ice skates, Portland, Maine is full of festive activities that make the holidays feel extra magical. Whether you’re strolling through charming streets decked out in lights, sipping cocoa at a cozy café, or exploring local art and holiday markets, there’s something for everyone to get in the holiday spirit.

Here are 3 things to do in Portland this holiday season to make your winter days merry and bright.

1. Admire the Christmas Trees + Lights

When night falls, the Old Port area of Portland transforms into a twinkling wonderland. Take a stroll and soak in the holiday lights and decorations. Don't miss the massive Christmas tree at Monument Square and the quirky lobster trap tree in front of the Portland Regency Hotel & Spa.

2. Discover Treasures at The Maker's Market

Got gifts to buy? The Maker's Market at Thompson's Point is your go-to spot on select Sundays from 10 AM to 3 PM before the holidays. Local artists and crafty folks gather here, offering all kinds of cool stuff like candles, maple syrups, jams, jewelry, knitwear, and even funky t-shirts.

Address: Brick South,15 Resurgam Place, Portland, ME

Cost: Free parking and entry!

3. Glide and Twirl on the Ice

If you dig winter activities, you'll adore ice skating. After you've checked out the market, head over to The Rink at Thompson's Point. It's an outdoor ice skating rink right nearby with awesome river views. You can skate your heart out and warm up in cozy spots with drinks and snacks.

Tips for Ice Skating at Thompson’s Point

Rentals: Skates are available to rent on-site, so no need to bring your own.
Timing: Arrive early to avoid crowds, especially on weekends or during evening hours.
Dress Warmly: Layer up—gloves, hats, and scarves are essential for outdoor skating.
Photos: The rink is especially picturesque at dusk, when lights reflect on the ice—perfect for Instagram shots!

And if you're looking to escape the city buzz, there are more ice skating options around Portland. Check out the outdoor skating ponds at 20 Municipal Drive in Scarborough, not far from Portland.

Note: Make sure to verify the ice status on the Town of Scarborough website.

So, whether you're up for the lights, the market, or some cool ice skating, Portland's got you covered this holiday season. Get out there and have a blast!

Thanks for reading!

- The Maine Chick