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Winter holiday events in Winslow, ME

Jonathan Sarty and The DellaValla Trio Home For the Holidays
Sat, Dec 20, 7:00 PM
Jackson · Wildcat Inn & Tavern
Jonathan Sarty and The DellaValla Trio Home For the Holidays
Sat, Dec 20, 7:00 PM
Jackson · Wildcat Inn & Tavern
Kennebunkport Christmas Prelude Trolley Rides
Friday at 9:30 AM + 83 more
Kennebunkport · Seashore Trolley Museum
Kennebunkport Christmas Prelude Trolley Rides
Friday at 9:30 AM + 83 more
Kennebunkport · Seashore Trolley Museum
Festive Glow: Holiday Spa Night
Wed, Dec 10, 4:00 PM
Kennebunkport · Tree Spa Pop-Up at Cape Arundel Inn & Resort Club House
Festive Glow: Holiday Spa Night
Wed, Dec 10, 4:00 PM
Kennebunkport · Tree Spa Pop-Up at Cape Arundel Inn & Resort Club House
Christmas Candle-Making Workshop at Sea Dog Brewing Co.
Thu, Dec 18, 6:00 PM
Conway · Sea Dog Brewing Company
Christmas Candle-Making Workshop at Sea Dog Brewing Co.
Thu, Dec 18, 6:00 PM
Conway · Sea Dog Brewing Company
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
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
Holiday Cocktail Class
Thu, Dec 11, 6:30 PM
Lyman · 52 S Waterboro Rd
Holiday Cocktail Class
Thu, Dec 11, 6:30 PM
Lyman · 52 S Waterboro Rd
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
Apéro Presents: Holiday Cookie Decorating with Whisked Away Bakery
Sun, Dec 7, 4:00 PM
Biddeford · Apéro
Apéro Presents: Holiday Cookie Decorating with Whisked Away Bakery
Sun, Dec 7, 4:00 PM
Biddeford · Apéro
James Montgomery Band / January 22nd, 2026
Thu, Jan 22, 7:00 PM
Jackson · Wildcat Inn & Tavern
James Montgomery Band / January 22nd, 2026
Thu, Jan 22, 7:00 PM
Jackson · Wildcat Inn & Tavern
Fire & Ice Friday Night with The Jim Ciampi Band!
Fri, Dec 12, 6:00 PM
Kennebunkport · Nonantum Resort
Fire & Ice Friday Night with The Jim Ciampi Band!
Fri, Dec 12, 6:00 PM
Kennebunkport · Nonantum Resort
Selling quickly
5th Annual Christmas Show
Wed, Dec 10, 5:00 PM
Kennebunkport · The Town House School
Selling quickly
5th Annual Christmas Show
Wed, Dec 10, 5:00 PM
Kennebunkport · The Town House School
Fire & Ice Saturday Night with Motor Booty Affair!
Sat, Dec 13, 6:00 PM
Kennebunkport · Nonantum Resort
Fire & Ice Saturday Night with Motor Booty Affair!
Sat, Dec 13, 6:00 PM
Kennebunkport · Nonantum Resort
Selling quickly
MWV Free! North Conway Tennis PLUS - Winter 2025
Wed, Nov 5, 3:30 PM
Conway · 78 Norcross Cir
Selling quickly
MWV Free! North Conway Tennis PLUS - Winter 2025
Wed, Nov 5, 3:30 PM
Conway · 78 Norcross Cir
Sales end soon
Deck the Stockings: Captain's Christmas Workshop
Friday at 12:00 PM
Kennebunkport · Kennebunkport Captains Collection
Sales end soon
Deck the Stockings: Captain's Christmas Workshop
Friday at 12:00 PM
Kennebunkport · Kennebunkport Captains Collection
MWV AK Match Play North Conway - Winter 2025
Thu, Nov 13, 3:30 PM
Conway · 78 Norcross Cir
MWV AK Match Play North Conway - Winter 2025
Thu, Nov 13, 3:30 PM
Conway · 78 Norcross Cir
Nearly full
Garnish & Garland Mixology
Fri, Dec 12, 2:00 PM
Kennebunkport · Earth at Hidden Pond
Nearly full
Garnish & Garland Mixology
Fri, Dec 12, 2:00 PM
Kennebunkport · Earth at Hidden Pond
Holiday Charm Bracelet Making
Sun, Dec 7, 12:00 PM
Kennebunkport · Kennebunkport Captains Collection
Holiday Charm Bracelet Making
Sun, Dec 7, 12:00 PM
Kennebunkport · Kennebunkport Captains Collection
Holly Jolly Mixology
Sat, Dec 6, 2:00 PM
Kennebunkport · Earth at Hidden Pond
Holly Jolly Mixology
Sat, Dec 6, 2:00 PM
Kennebunkport · Earth at Hidden Pond
Holiday Cocktail Class at The Burleigh
Sat, Dec 20, 1:00 PM
Kennebunkport · The Burleigh
Holiday Cocktail Class at The Burleigh
Sat, Dec 20, 1:00 PM
Kennebunkport · The Burleigh

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