Visit MaineToday's profile on Pinterest.

About The Author


Shannon Bryan

Send an email | Read more from Shannon

Posted: December 1, 2013

Santacon, Santa Surf & Sedaris: 8 things to do in Southern Maine this weekend

Written by: Shannon Bryan

The theme this weekend (and perhaps for the next 20 days) is Santa. And while we’re used to a Santa who sits in a big chair at the mall all December while kindly pretending to give a hoot about our Christmas wishes, the Santas we’ll be seeing this weekend are, well, a more lively sort. Santacon, the annual Santa bar crawl, takes place in Portland on Saturday. And Surfrider’s Maine chapter is rounding up Santas on surfboards down in Kennebunkport. In Freeport, runners can dress up in holiday garb for a Santa-themed sprint through town. And you’re welcome to dress up as the big mad in red for any other weekend activities, like First Friday Art Walk, The Santaland Diaries, and any of the classic holiday festivals happening in towns around Southern Maine.

For the weekend of Dec 5-8

1. Love the holiday curmudgeon

Press Herald file photo

The Santaland Diaries

7:30 Friday & Saturday, 2 pm Saturday & Sunday | Portland Stage, Studio Theatre, Portland | $25, students $20 |
Spend an irreverent evening with Crumpet – one of Santa’s little helpers during the holiday rush at Macy’s – as he copes with thousands of shoppers (and their kiddies) with whacked out, wicked wit. This show is a holiday treat for grownups, so leave the little angels at home for a behind-the-scenes peek at an elf gone bad. For mature elves only!

2. Art walk, art shop

MECA Holiday Sale graphic

MECA Holiday Sale

Friday-Sunday | Maine College of Art, Portland |
Give the gift of original art. Find the perfect gift, crafts, and fine arts by MECA students, alumni, faculty and staff. Shop, connect with the arts, and buy local. Free admission.

Goodwill’s Art for Everyone sale

5-8 pm Friday | Cathedral Church of St. Luke in Portland |
Art. Affordable art. Yep, it exists! This event features a collection of donated art for sale at affordable prices for every budget. Over 200 pieces of artwork donated to Goodwill stores have been curated, including: oils, watercolors, drawings, mixed media, and prints. This collection is selected from donations via our 27 retail stores in Maine, New Hampshire, and Vermont. Proceeds from this fundraiser benefit Goodwill services across New England

Art on the Hill SEA Holiday Art Sale

Friday-Sunday | East End Community School, Portland |
Over 80 local artists and an incredible weekend of holiday shopping! There’ll be something for everyone on your shopping list at this three-day event.

3. Spread Christmas Cheer. And drink beer.

Press Herald file photo


Starting at 4 pm Saturday | Various bars, Portland (starts at Pat’s Pizza, Portland) | Free |
Hundreds of Santas, Mrs. Clauses, Rudolphs, Mistletoes, Christmas trees, Abominable Snowmen and Elves turn out for a festive bar crawl.

4. Surf like Santa photo

Santa Surf and beach cleanup

10 am Saturday | Gooch’s Beach, Kennebunkport | $10 donation |
Dress up as Santa and hit the waves at Gooch’s Beach. Surfers, swimmers, bodyboarders, paddleboarders welcome. Enjoy raffles, cookies, hot drinks, and a costume contest, too.

5. Celebrate Christmas in classic style

Press Herald file photo

Dec 5-15: Christmas Prelude

Thursday-December 15 | Kennebunkport |
You know those utopian-looking holiday cards depicting a New England Christmas with carriage rides, giant trees draped in white lights and cheery, rosy-cheeked townspeople sipping hot cocoa and peering into downtown shop windows? Yea, Prelude in Kennebunkport is kinda like that. Except the carriage rides are really jaunts in an historic electric streetcar, one of the decorated trees is made out of lobster traps, and the hot cocoa might be a cocktail. There are craft fairs, chowder supper, string quartets, Christmas karaoke, and bonfires.

6. Meet the talking Christmas tree

Sparkle Weekend photo

20th Annual Sparkle Weekend

Friday-Sunday | Downtown Freeport | Many activities free |
Parade of lights, Musical Holiday Light Show, Free Holiday Movie – The Polar Express, Free Old-Fashioned Horse Drawn Wagon Rides, Visits with Santa, meet real sled dogs, Holiday Caroling, MORE

7. Decorate cookies, meet Santa, shop local crafts

Holiday Festival promotional graphic

Downtown Holiday Festival & Anti-Freeze Craft Fair

5-7 pm Friday & all day Saturday | Downtown Biddeford | Many activities free |
A live ice-carving show, storytellers, musicians and maybe even dancing vegetables will entertain from 5 to 7 pm in City Square, and Santa himself will travel by horse-drawn sleigh to City Square to light the tree at 5:30 pm. Also that evening: photos with Santa at Joseph McKenney Photography Studio (photos by donation), free horse-drawn sleigh rides, cookie decorating at Reilly’s bakery, and concessions provided by La Kermesse. On Saturday: Holiday short movies will be shown for free in City Theater from 1 to 3 pm. The Anti-Freeze Winter Arts & Crafts fair will take place from 9:30 am to 3 pm on Saco Island, and the Oak + the Ax will feature a craft fair at 140 Main Street.

8. Run with Santa-like speed. Dressed as Santa.

Freeport Jingle Bell Run

10 am Sunday Freeport High School, Freeport and Hermon Elementary School, Hermon | $30 for ages 10 and up, $15 for 10 and under |
There’s running, as expected, but to run this 5k, you should be decked out in holiday attire. Embrace the costuming. These runs help raise funds for the Arthritis Foundation.

Up Next: