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Winter holiday events in Naples, ME

Downeasters Chorus 2025 Holiday Show
Mon, Dec 15, 7:00 PM
Yarmouth · 317 Main Community Music Center
Downeasters Chorus 2025 Holiday Show
Mon, Dec 15, 7:00 PM
Yarmouth · 317 Main Community Music Center
Holiday Wreath Making Workshop at Flight Deck Brewing
Tue, Dec 9, 5:00 PM
Brunswick · Flight Deck Brewing
Holiday Wreath Making Workshop at Flight Deck Brewing
Tue, Dec 9, 5:00 PM
Brunswick · Flight Deck Brewing
321 Reindeer Games
Sat, Dec 13, 8:00 AM
Topsham · CrossFit 321
321 Reindeer Games
Sat, Dec 13, 8:00 AM
Topsham · CrossFit 321
Fireside Igloo Rentals at Captain's Christmas
Friday at 11:00 AM + 19 more
Kennebunkport · Kennebunkport Captains Collection
Fireside Igloo Rentals at Captain's Christmas
Friday at 11:00 AM + 19 more
Kennebunkport · Kennebunkport Captains Collection
Breakfast with Santa
Sat, Dec 20, 10:00 AM
Freeport · Freeport High School
Breakfast with Santa
Sat, Dec 20, 10:00 AM
Freeport · Freeport High School
Maine Public Holiday Paint and Sip Night
Sun, Dec 7, 6:00 PM
Portland · Rising Tide Brewing Company
Maine Public Holiday Paint and Sip Night
Sun, Dec 7, 6:00 PM
Portland · Rising Tide Brewing Company
Sales end soon
Gingerbread House Making: An Adults-Only Holiday Night Out
Thursday at 5:00 PM
Kennebunkport · Kennebunkport Captains Collection
Sales end soon
Gingerbread House Making: An Adults-Only Holiday Night Out
Thursday at 5:00 PM
Kennebunkport · Kennebunkport Captains Collection
Jud Caswell's Holiday Show
Sat, Dec 20, 7:00 PM
Freeport · Cadenza
Jud Caswell's Holiday Show
Sat, Dec 20, 7:00 PM
Freeport · Cadenza
Sales end soon
Winter Cardinal Paint Party - Dec. 2 - 6-8:30PM - Gardiner Elks Lodge
Tuesday at 6:00 PM
Gardiner · Gardiner Elks Lodge
Sales end soon
Winter Cardinal Paint Party - Dec. 2 - 6-8:30PM - Gardiner Elks Lodge
Tuesday at 6:00 PM
Gardiner · Gardiner Elks Lodge
Paint Night with Hannah Tauroney
Wed, Dec 17, 6:00 PM
Windham · Eriks Church
Paint Night with Hannah Tauroney
Wed, Dec 17, 6:00 PM
Windham · Eriks Church
Holiday Charm Bracelet Brunch
Sun, Dec 21, 11:30 AM
Portland · Blind Tiger Portland – Danforth Street
Holiday Charm Bracelet Brunch
Sun, Dec 21, 11:30 AM
Portland · Blind Tiger Portland – Danforth Street
Selling quickly
Holiday Showcase: Taste, Sip & Meet the Makers - Session 1
Sun, Dec 14, 5:30 PM
Portland · Sissle & Daughters Cheesemongers and Grocers (Formerly The Cheese Shop of Portland)
Selling quickly
Holiday Showcase: Taste, Sip & Meet the Makers - Session 1
Sun, Dec 14, 5:30 PM
Portland · Sissle & Daughters Cheesemongers and Grocers (Formerly The Cheese Shop of Portland)
UNHOLY NIGHT on Christmas Eve Eve at Rumors!
Tue, Dec 23, 8:00 PM
Biddeford · Rumors
UNHOLY NIGHT on Christmas Eve Eve at Rumors!
Tue, Dec 23, 8:00 PM
Biddeford · Rumors
The Holiday Party with Maine Women in Business
Tue, Dec 16, 6:00 PM
Biddeford · The Lincoln Hotel
The Holiday Party with Maine Women in Business
Tue, Dec 16, 6:00 PM
Biddeford · The Lincoln Hotel
Sales end soon
Gingerbread House Decorating Class (for the Adults!)
Sun, Dec 7, 1:00 PM
Gray · Caswell Farm & Wedding Barn
Sales end soon
Gingerbread House Decorating Class (for the Adults!)
Sun, Dec 7, 1:00 PM
Gray · Caswell Farm & Wedding Barn
Nearly full
A Cold River Radio Christmas Season Finale!
Sun, Dec 14, 6:00 PM
Conway · Majestic Theatre
Nearly full
A Cold River Radio Christmas Season Finale!
Sun, Dec 14, 6:00 PM
Conway · Majestic Theatre
Adult Story Time with THEM Burlesque | Smutty Holidays
Fri, Dec 19, 8:00 PM
Portland · Novel
Adult Story Time with THEM Burlesque | Smutty Holidays
Fri, Dec 19, 8:00 PM
Portland · Novel
Nearly full
Christmas Themed Murder/Mystery Dinner at WillowsAwake Winery
Fri, Dec 19, 6:00 PM
Leeds · WillowsAwake Winery and No.10 Eatery
Nearly full
Christmas Themed Murder/Mystery Dinner at WillowsAwake Winery
Fri, Dec 19, 6:00 PM
Leeds · WillowsAwake Winery and No.10 Eatery
Winter Solstice w/Taylor O'Donnell
Sun, Dec 21, 5:00 PM
Kittery · The Dance Hall
Winter Solstice w/Taylor O'Donnell
Sun, Dec 21, 5:00 PM
Kittery · The Dance Hall
Sales end soon
"Festive Snowman", a BYOB PAINT & SIP EVENT with Lisa
Thursday at 6:00 PM
Waterville Valley · Golden Eagle Lodge Resort
Sales end soon
"Festive Snowman", a BYOB PAINT & SIP EVENT with Lisa
Thursday at 6:00 PM
Waterville Valley · Golden Eagle Lodge Resort

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