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Southern Maine Guide to Holiday Events

In November and December,  Southern Maine comes alive with a special kind of holiday enchantment. Join Portside as we explore the coastal towns and charming communities that transform into idyllic winter wonderlands during the holiday season.


November 24-28
Fosters Clambake, York

Kick of the holiday season by taking in the beauty of festively decorated Christmas Trees! This year, Portside is one of many community members donating a tree that will be auctioned off to raise money to support young Maine adults (18+) that are aging out of the foster care system.


Sat, Dec 2
Central School Gym, South Berwick

Downtown South Berwick lights up with holiday cheer for their annual “Home for the Holidays” celebration.  Portside will be participating in the Craft Fair and offering participants of all ages the opportunity to create a holiday ornament of their very own.  We look forward to seeing you there!



Nov. 30th - Dec. 10th 
Multiple Dates + Various Locations

Picture a Hallmark Christmas movie coming to life: The festive lights, the greenery, the towering tree in the center of the square, the community coming together.

The good news is that the world doesn’t only exist in the movies: You can experience it in Kennebunkport each year during Christmas Prelude.

Tree lightings, Santa arriving by lobster boat, caroling at the Franciscan Monastery, a beautiful fireworks display, a lively street festival, and more are just some of the highlights of the 11-day event. So make Christmas part of your holiday traditions and watch the magic come alive!


Multiple Dates + Times 
The Grant Hotel, Kennebunk

Join Portside Real Estate Group for fun-filled holiday activities designed especially for KIDS. Let your child's imagination run wild while making a holiday-inspired craft of their choice.  On your way out the door, grab a Prelude-themed scavenger hunt to complete as you explore the town! This donation-based event and 100% of the proceeds will benefit Grahamtastic Connections!


Friday, December 8th
Portside is a proud sponsor of this years Christmas Prelude Fireworks display! Gather near the cove on the townline of Kennebunk and Kennebunkport on Friday, December 8th to view this festive fireworks display! 



Friday - Sunday, Dec 1st-3rd and 8th-10th
Multiple Dates + Various Times
Seashore Trolley Museum, 195 Log Cabin Road Kennebunkport, ME 04046

Come out to the Seashore Trolley Museum for a special winter treat! Ride in heated trolleys decked out in live holiday greens on our private heritage railroad, enjoy delicious hot chocolate and our outdoor fire pit and marshmallows or s'mores, warm up in our Exhibit Room with a large gingerbread house on display and gingerbread-themed crafts for youth and youth at heart, enjoy live music, and find great deals in our Museum Store!



Sat. Dec 16th - Sat. Dec 23rd 
Various Times + Multiple Venues 

Portland Ballet’s A Victorian Nutcracker returns to the stage this holiday season with newly designed backdrops and set pieces inspired by Portland’s Victoria Mansion. A Victorian Nutcracker is a retelling of the classic story of a young girl’s Christmas Eve dream, brought on by the curious gift of a nutcracker, in which she travels to the Sugar Plum Fairy’s Land of the Sweets. This version, with characters pulled directly from Portland’s past, is sure to please audience members of all ages.



Fri, Dec 8th, - Sun, Dec 17th
Various Times 
Merrill Auditorium, 20 Myrtle St, Portland, ME

Enjoy this cherished Maine holiday tradition (now in its 44th year!) Join your Portland Symphony to celebrate the season with Christmas classics new and old – including the beloved “Sleigh Ride”!

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