Last year’s Christmas tree in Monument Square was a 50-foot blue spruce. This year, the city of Portland will hold its tree lighting ceremony on Friday, Nov. 29. Brianna Soukup / Portland Press Herald

Municipal holiday events in Greater Portland are credited with boosting the local economy, affirming the spirit of community and bringing light to the increasingly dark days of winter. Events coming to the region include the Monument Square tree lighting in Portland, the Ugly Sweater 5K and Merry Mile Fun Run in Falmouth, and breakfast with Santa in Cumberland.

Executive director of Portland Downtown Cary Tyson said the winter holidays are arguably Downtown Portland’s busiest season. The organization facilitates a variety of holiday events for the community that benefit the local economy.

“We’re a big believer of shopping local. This is a big commercial time of the year when folks are out participating in commerce. So, we really want to encourage that local shopping, visiting our local spaces, because that’s what makes Portland unique, and it also sort of helps reinforce the vibrancy of the place as well,” said Tyson.

Increased foot traffic from holiday shoppers in Portland-area communities supports local businesses instead of online and national chain retailers. Business groups that advocate for shopping locally point to multiple benefits: improved local economies, as 53% of revenue from independent retailers is recirculated locally, as compared to 14% from national chain retailers; creating jobs by shopping at local businesses; benefits to local tax revenue; environmental sustainability; and increases in community and civic engagement.

“Visiting the local shops, craft shows and restaurants during the holidays is one of the highlights of living … here in Maine. We’re lucky to have so many local businesses to choose from in our communities,” Amy Landry, board president of Portland Buy Local, wrote in an email.

“And if we want that festive, bustling atmosphere to continue, we must continue to choose local first,” she wrote.

Some of these events have a very long tradition – the city of Portland has placed Christmas trees in Monument Square since 1939 or earlier – while others are new. Regardless, the festive events all come together to create a sense of identity in the region.

“Downtown Portland is some place, it’s not any place,” said Tyson.

See below local municipal events in the Greater Portland area this holiday season:

CAPE ELIZABETH

The fifth annual tree lighting will take place on the Town Green. Friday, Dec. 6, 6-7 p.m. Free.

A Cape Elizabeth Holiday Market will feature over 10 vendors and local Maine artists with treats and creations for sale. Saturday, Dec. 14, 10 a.m.-4 p.m. Free. United Methodist Church, 280 Ocean House Road, Cape Elizabeth.

CUMBERLAND

Annual breakfast with Santa is an opportunity to take a photo with Santa and have a pancake breakfast. Proceeds from the event will go toward buying gifts for families in need this holiday season. A toy drive collection box will also be at the door. Sunday, Dec. 1, 7 a.m. Adults $12, kids $8. Greely Middle School, 351 Tuttle Road, Cumberland.

A Holiday Celebration by Active Living 55+ will feature refreshments, holiday music from the Greely Madrigal Singers and a holiday reading. Thursday, Dec. 19, 10 a.m.-12:30 p.m. Free. Cumberland Crossing, Cumberland.

Christmas Day lunch will be hosted for the second year by Active Living 55+. Celebrate Christmas Day together with a luncheon. Wednesday, Dec. 25, noon-2 p.m. RSVP required, email dgalvan@cumberlandmaine.com. Val Halla Golf and Recreation, 60 Val Halla Road, Cumberland. 

FALMOUTH

Falmouth’s 38th annual community tree lighting is taking place at Village Park, hosted by Falmouth Parks and Community Programs. Special guests from the North Pole will arrive to light the tree. Thursday, Dec. 5, 5:30-6:30 p.m. Free. Village Park, Hat Trick Drive, Falmouth.

The Merry Mix and Mingle and fireworks is an open-air community party with music, cookies and warm beverages, kids’ activities and a photo booth. View a festive fireworks display at 7 p.m. Friday, Dec. 6, 6-8 p.m. Free. American Legion Post 164, 65 Depot Road, Falmouth.

Ugly Sweater 5K and Merry Mile Fun Run will be a blur of color on Route 1 as participants race in festive sweaters. There is both a 5K chip-timed road race and a 1-mile fun walk. Proceeds benefit Falmouth Memorial Library. Saturday, Dec. 7, 9 a.m. Registration required. Depot Road to Route 1, Falmouth.

PORTLAND

Monument Square tree lighting is an annual tradition in the heart of Portland. The family-friendly event begins with a princess and superhero meet-and-greet, followed by an outdoor movie watch party with complimentary eggnog tastings. Enjoy live dance and music performances at 3:30 p.m., with the tree illuminating around 4:30 p.m. Friday, Nov. 29, 1-5:30 p.m. Free. Monument Square, Portland.

The Christmas Ship Parade will fill the Portland Harbor with boats decked out in Christmas lights and costumed passengers. Saturday, Dec. 14, 4:30 p.m. Free (registration required for participating boats). Portland Waterfront, Portland.

SCARBOROUGH

Letters to Santa can be dropped at the North Pole Express mailbox in front of Town Hall. If letters are received before Monday, Dec. 2, children will receive a reply from Santa by mail. Through Dec. 25. Free. Town Hall or P.O. Box 360, Scarborough, ME 04074.

Gingerbread House Night 2024 will provide house kits, icing, plus music, coloring tables and light refreshments. Friday, Dec. 13, 6:30-8 p.m. Registration required, $8 per house. Wentworth School Cafeteria, 20 Quentin Drive, Scarborough.

SOUTH PORTLAND

Holiday tree lighting in Mill Creek Park will be a festive evening filled with speakers, poetry and singing leading up to the lighting of the tree. Friday, Dec. 6, 4:30-6:30 p.m. Free. Mill Creek Park, 50 Hinckley Drive, South Portland.

WESTBROOK

Holiday Market and Celebration at Westbrook Common will have hot chocolate and s’mores, a local makers’ market and live music. Saturday, Dec. 7, 4-7 p.m. Free. Westbrook Common. 

YARMOUTH

Light Up Yarmouth brings light to Yarmouth throughout December, as local residents, organizations and businesses decorate their buildings with lights of all patterns, shapes and colors. Drive around following a map of participating Yarmouth locations to see the full display. Through Dec. 31. Free. yarmouthcommunityservices.org

Editor’s note: This story was updated at 12:57 on 12/4/2024 to correct the date of the Ugly Sweater 5K and Merry Mile Fun Run. It is on December 7, not December 9.