20 mi

Santa's Magical Trolley Ride

Sat, Nov 28 · 10:00 AM

Seashore Trolley Museum · Kennebunkport

$25

See details

0.4 mi

Rigometrics - Rigsmas 2026

Fri, Dec 11 · 7:00 PM

Live at Madrid's · Portland

$20 advance

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0.3 mi

Weakened Friends - New Years Eve 2026! w/ Rebuilder & Freak Phone

Thu, Dec 31 · 9:00 PM

Portland House of Music and Events · Portland

$30 advance / $40 day of show

See details

0.2 mi

State Street Church Holiday Fair & Lunch

Saturday · 9:00 AM

State Street Church · Portland

Free

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0.9 mi

Annual Celtic Fair 2026

Saturday · 9:00 AM

Maine Irish Heritage Center · Portland

Free

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1.6 mi

Winter Wonderland Christmas Fair

Saturday · 9:00 AM

310 Broadway, South Portland · South Portland

Free

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15 mi

Fall Fair at Saco Grange #53

Saturday · 9:00 AM

Saco Grange #53 · Saco

Free

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23 mi

Holy Spirit Parish Holiday Fair

Saturday · 9:00 AM

St. Martha Church · Kennebunk

See details

3.0 mi

Rosemont Artist Guild + Caravan Artist Market

Saturday · 10:00 AM

Breakwater School · Portland

Free

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9.7 mi

USM Fall Craft Show

Saturday · 10:00 AM

Costello Sports Complex, University of Southern Maine (USM) Gorham Campus · Gorham

Free

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12 mi

Women's Collective November Holiday Market

Saturday · 10:00 AM

Maine Sports Arena · Saco

Free

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23 mi

Cozy Holiday Market at Mare Brook Farm

Saturday · 10:00 AM

Mare Brook Farm · Brunswick

See details

24 mi

Whimsical Holiday Paper Dolls

Saturday · 10:00 AM

Brick Store Museum · Kennebunk

$25

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0.2 mi

A Drag Queen Christmas

Saturday · 8:00 PM

Merrill Auditorium · Portland

$63 / $48 / $33 before fees

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15 mi

Fall Fair at Saco Grange #53 (Day 2)

Sunday · 9:00 AM

Saco Grange #53 · Saco

Free

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9.7 mi

USM Fall Craft Show

Sunday · 10:00 AM

Costello Sports Complex, University of Southern Maine (USM) Gorham Campus · Gorham

Free

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1.9 mi

Friendsgiving!

Sunday · 4:00 PM

Bunker Brewing Co. · Portland

Free

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0.2 mi

State Street Church Holiday Fair & Lunch

Sat, Nov 14 · 9:00 AM

State Street Church · Portland

Free

See details

0.9 mi

Annual Celtic Fair 2026

Sat, Nov 14 · 9:00 AM

Maine Irish Heritage Center · Portland

Free

See details

1.6 mi

Winter Wonderland Christmas Fair

Sat, Nov 14 · 9:00 AM

310 Broadway, South Portland · South Portland

Free

See details

3.0 mi

Rosemont Artist Guild + Caravan Artist Market

Sat, Nov 14 · 10:00 AM

Breakwater School · Portland

Free

See details

9.7 mi

USM Fall Craft Show

Sat, Nov 14 · 10:00 AM

Costello Sports Complex, University of Southern Maine (USM) Gorham Campus · Gorham

Free

See details

12 mi

Women's Collective November Holiday Market

Sat, Nov 14 · 10:00 AM

Maine Sports Arena · Saco

Free

See details

15 mi

Fall Fair at Saco Grange #53

Sat, Nov 14 · 9:00 AM

Saco Grange #53 · Saco

Free

See details

23 mi

Cozy Holiday Market at Mare Brook Farm

Sat, Nov 14 · 10:00 AM

Mare Brook Farm · Brunswick

See details

23 mi

Holy Spirit Parish Holiday Fair

Sat, Nov 14 · 9:00 AM

St. Martha Church · Kennebunk

See details

24 mi

Whimsical Holiday Paper Dolls

Sat, Nov 14 · 10:00 AM

Brick Store Museum · Kennebunk

$25

See details

0.2 mi

A Drag Queen Christmas

Sat, Nov 14 · 8:00 PM

Merrill Auditorium · Portland

$63 / $48 / $33 before fees

See details

9.7 mi

USM Fall Craft Show

Sun, Nov 15 · 10:00 AM

Costello Sports Complex, University of Southern Maine (USM) Gorham Campus · Gorham

Free

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15 mi

Fall Fair at Saco Grange #53 (Day 2)

Sun, Nov 15 · 9:00 AM

Saco Grange #53 · Saco

Free

See details

1.9 mi

Friendsgiving!

Sun, Nov 15 · 4:00 PM

Bunker Brewing Co. · Portland

Free

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24 mi

Merrymeeting Tree Fest Preview Night

Thu, Nov 19 · 5:00 PM

YMCA at Brunswick Landing · Brunswick

See details

24 mi

Merrymeeting Tree Fest

Fri, Nov 20 · 10:00 AM

YMCA at Brunswick Landing · Brunswick

$2 admission

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16 mi

L.L.Bean Holiday Tree Lighting

Fri, Nov 20 · 4:00 PM

L.L.Bean Flagship Store — Discovery Park · Freeport

Free

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2.9 mi

Annual Makers Market Christmas Arts & Craft Show

Sat, Nov 21 · 9:00 AM

South Portland High School · South Portland

$3 admission

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16 mi

Freeport Lioness Lions – 28th Annual Holiday Craft Fair and Fish 'Chowdah' & Chili Luncheon

Sat, Nov 21 · 9:00 AM

Freeport Harraseeket Grange #9 · Freeport

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15 mi

Festival of Trees Preview Gala

Sat, Nov 21 · 12:00 AM

Saco Museum · Saco

Tickets on sale mid-October

See details

Winter Craft Fair at Ferry Beach Retreat & Conference Center

Sun, Nov 22 · 9:00 AM

Ferry Beach Retreat & Conference Center · Saco

Free

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6.2 mi

Scarborough Community Thanksgiving

Thu, Nov 26 · 11:00 AM

Wentworth School · Scarborough

Free

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0.5 mi

Christmas at Victoria Mansion

Fri, Nov 27 · 10:00 AM

Victoria Mansion · Portland

Ticket prices are the same as during the regular season

See details

6.6 mi

Home for the Holidays Craft Show

Fri, Nov 27 · 10:00 AM

Scarborough High School · Scarborough

Free

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15 mi

Saco Museum Festival of Trees

Fri, Nov 27 · 10:00 AM

Saco Museum · Saco

See details

0.2 mi

Maine State Ballet: The Nutcracker

Fri, Nov 27 · 2:00 PM

Merrill Auditorium · Portland

$23–$94

See details

L.L.Bean Black Friday Midnight Madness

Fri, Nov 27 · 12:00 AM

L.L.Bean Flagship Store · Freeport

See details

0.2 mi

Maine State Ballet: The Nutcracker

Sat, Nov 28 · 2:00 PM

Merrill Auditorium · Portland

$23–$94

See details

22 mi

Routine Holiday Social

Sat, Nov 28 · 4:00 PM

Routine · Brunswick

Free

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22 mi

Brunswick Annual Tree Lighting Ceremony

Sat, Nov 28 · 3:00 PM

Brunswick Town Mall · Brunswick

Free

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0.2 mi

Maine State Ballet: The Nutcracker

Sun, Nov 29 · 2:00 PM

Merrill Auditorium · Portland

$23–$94

See details

0.5 mi

Stories on the Staircase

Mon, Nov 30 · 11:00 AM

Victoria Mansion · Portland

Free

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20 mi

Christmas Prelude in the Model Railroad Building

Thu, Dec 3 · 9:30 AM

Seashore Trolley Museum · Kennebunkport

$5 per person, at the door only

See details

24 mi

45th Annual Christmas Prelude

Thu, Dec 3 · 10:00 AM

Kennebunkport (town-wide) · Kennebunkport

Free

See details

0.5 mi

2026 Holiday Gala

Thu, Dec 3 · 5:00 PM

Victoria Mansion · Portland

See details

24 mi

Candlelight Christmas Party at White Columns

Thu, Dec 3 · 6:00 PM

White Columns · Kennebunkport

$81.88 (Eventbrite, with fees)

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24 mi

Gingerbread House Making: An Adults-Only Holiday Night Out

Thu, Dec 3 · 6:00 PM

Kennebunkport Captains Collection · Kennebunkport

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20 mi

Christmas Prelude Trolley Rides

Fri, Dec 4 · 10:00 AM

Seashore Trolley Museum · Kennebunkport

$15

See details

0.7 mi

Copper Beech Tree Lighting

Fri, Dec 4 · 4:00 PM

Portland Museum of Art · Portland

Free

See details

0.7 mi

Beech Tree Bazaar

Fri, Dec 4 · 4:00 PM

Portland Museum of Art · Portland

Free

See details

15 mi

Saco Holiday Tree Lighting

Fri, Dec 4 · 4:00 PM

Saco Transportation Center · Saco

Free

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15 mi

Downtown Menorah Lighting

Fri, Dec 4 · 4:30 PM

Downtown Biddeford · Biddeford

Free

See details

0.4 mi

Jay Braggs Christmas In New Vaudeville

Fri, Dec 4 · 8:00 PM

Live at Madrid's · Portland

$25 general admission

See details

0.4 mi

THE POLAR EXPRESS Train Ride

Fri, Dec 4 · 12:00 AM

Ocean Gateway Marine Terminal · Portland

Coach $35 / First Class $65 / Presidential $105 per person (peak dates higher)

See details

0.7 mi

MECA&D Holiday Sale

Fri, Dec 4 · 5:00 PM

Maine College of Art & Design · Portland

Free

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15 mi

Merry & Bright Night

Fri, Dec 4 · 5:30 PM

Downtown Biddeford (City Square) · Biddeford

Free

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16 mi

Sparkle Celebration Parade of Lights

Fri, Dec 4 · 6:45 PM

Downtown Freeport — Main Street & Bow Street · Freeport

Free

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16 mi

33rd Annual Sparkle Celebration

Fri, Dec 4 · 12:00 AM

Downtown Freeport · Freeport

Free

See details

23 mi

Cape Porpoise Lobster Trap Tree Lighting

Fri, Dec 4 · 7:00 PM

Cape Porpoise Square · Kennebunkport

Free

See details

24 mi

Tree Lighting Ceremony in Dock Square

Fri, Dec 4 · 5:30 PM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

15 mi

Saco Main Street Holiday Festival and Parade of Lights

Sat, Dec 5 · 10:00 AM

Downtown Saco · Saco

Free

See details

15 mi

Saco Holiday Festival

Sat, Dec 5 · 10:00 AM

Saco Main Street · Saco

Free

See details

15 mi

Family Ornament Painting Workshop

Sat, Dec 5 · 10:00 AM

Mill Studio Arts · Biddeford

$85 per family

See details

23 mi

Holiday Book & Art Sale

Sat, Dec 5 · 9:30 AM

Louis T. Graves Memorial Public Library · Kennebunkport

Free

See details

0.2 mi

Maine State Ballet: The Nutcracker (matinee)

Sat, Dec 5 · 2:00 PM

Merrill Auditorium · Portland

$23–$94

See details

20 mi

Festival of Lights Parade

Sat, Dec 5 · 4:30 PM

York Village · York

Free

See details

24 mi

21st Annual Hat Parade

Sat, Dec 5 · 3:00 PM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

24 mi

Reindeer & Mrs. Claus at Kennebunk Outfitters

Sat, Dec 5 · 2:30 PM

Kennebunk Outfitters · Kennebunk

Free

See details

0.2 mi

It's a Wonderful Life: A Live Radio Play

Sat, Dec 5 · 7:30 PM

Portland Stage · Portland

Pay what you can

See details

0.3 mi

Gary Ho Ho Hoey's Rockin' Holiday Show!

Sat, Dec 5 · 8:00 PM

Portland House of Music and Events · Portland

$30 standing advance / $35 standing day of show

See details

0.7 mi

Advance Base with Karima Walker and Lisa/Liza

Sat, Dec 5 · 8:00 PM

SPACE · Portland

See details

24 mi

Christmas Candlelight Caroling

Sat, Dec 5 · 6:30 PM

St. Anthony's Monastery, Our Lady of Lourdes Grotto · Kennebunk

Free

See details

2.0 mi

Sea Spray @ Holiday Maker's Market '26

Sun, Dec 6 · 10:00 AM

Thompson's Point — Brick South · Portland

See details

0.8 mi

A Charlie Brown Christmas with The Heather Pierson Trio

Sun, Dec 6 · 4:00 PM

One Longfellow Square · Portland

$35 advance / $40 day of show

See details

24 mi

Wave to Santa On the Lobster Boat

Sun, Dec 6 · 12:30 PM

Mathew Lanigan Bridge, Dock Square · Kennebunkport

Free

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24 mi

Santa Arrives by Lobster Boat

Sun, Dec 6 · 1:00 PM

Nonantum Resort · Kennebunkport

Free

See details

24 mi

Make your own holiday succulent arrangement

Wed, Dec 9 · 5:00 PM

Alisson's Restaurant · Kennebunkport

$33.85–$49.87 (Eventbrite, with fees)

See details

24 mi

Festive Glow: Holiday Spa Night

Wed, Dec 9 · 6:00 PM

Tree Spa Pop-Up at Cape Arundel Inn & Resort Club House · Kennebunkport

$55.20 (Eventbrite, with fees)

See details

24 mi

Mid-Week Music: Christmas Show

Wed, Dec 9 · 5:00 PM

Town House School · Kennebunkport

$28.52 (Eventbrite, with fees)

See details

20 mi

Christmas Prelude in the Model Railroad Building

Thu, Dec 10 · 9:30 AM

Seashore Trolley Museum · Kennebunkport

$5 per person, at the door only

See details

22 mi

Storybook Christmas at Kennebunkport Conservation Trust

Thu, Dec 10 · 4:00 PM

Kennebunkport Conservation Trust · Kennebunkport

Free

See details

0.8 mi

Portland Jazz Orchestra Holiday Show (2 nights)

Thu, Dec 10 · 8:00 PM

One Longfellow Square · Portland

$25 advance / $30 day of show

See details

20 mi

Christmas Prelude Trolley Rides (Second Weekend)

Fri, Dec 11 · 9:30 AM

Seashore Trolley Museum · Kennebunkport

$15 per person

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Fri, Dec 11 · 2:00 PM

Merrill Auditorium · Portland

$28–$101

See details

24 mi

Prelude Family Street Festival

Fri, Dec 11 · 4:00 PM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Fri, Dec 11 · 7:00 PM

Merrill Auditorium · Portland

$28–$101

See details

15 mi

A Christmas Story: The Musical (Dec 11)

Fri, Dec 11 · 7:30 PM

City Theater · Biddeford

$30 - $35

See details

23 mi

Frost & Follies

Fri, Dec 11 · 12:00 AM

The Theater Project · Brunswick

Ticketed

See details

24 mi

Tree Lighting Ceremony in Dock Square (Second Weekend)

Fri, Dec 11 · 5:30 PM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

24 mi

15th Annual Christmas Fireworks Display

Fri, Dec 11 · 6:15 PM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

15 mi

Christmas Fair at Saco Grange #53

Sat, Dec 12 · 9:00 AM

Saco Grange #53 · Saco

Free

See details

15 mi

Merry Makers Craft Show

Sat, Dec 12 · 9:00 AM

75 Franklin Street · Saco

Free

See details

15 mi

Sparkle Celebration Frosty Frolic

Sat, Dec 12 · 10:00 AM

Freeport Village Station · Freeport

Free

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sat, Dec 12 · 2:00 PM

Merrill Auditorium · Portland

$28–$101

See details

24 mi

Reindeer & Mrs. Claus at Kennebunk Outfitters (Session 2)

Sat, Dec 12 · 2:30 PM

Kennebunk Outfitters · Kennebunk

Free

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sat, Dec 12 · 7:00 PM

Merrill Auditorium · Portland

$28–$101

See details

0.7 mi

Strut Krampus: Portland's Queer Holiday Ritual

Sat, Dec 12 · 8:00 PM

SPACE · Portland

$30 early bird / $35–$40 / $45 day of show

See details

15 mi

Girls' Night In at Saco Grange #53

Sat, Dec 12 · 5:00 PM

Saco Grange #53 · Saco

Free

See details

24 mi

Saturday Fire & Ice: Gone Fishing with Hello Newman

Sat, Dec 12 · 6:00 PM

Nonantum Resort · Kennebunkport

$100 general admission ($108.55 on Eventbrite with fees)

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sun, Dec 13 · 11:00 AM

Merrill Auditorium · Portland

$28–$101

See details

24 mi

16th Annual Pooch Parade

Sun, Dec 13 · 11:00 AM

Dock Square, Kennebunkport · Kennebunkport

Free

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sun, Dec 13 · 3:00 PM

Merrill Auditorium · Portland

$28–$101

See details

15 mi

A Christmas Story: The Musical (Dec 13 matinee)

Sun, Dec 13 · 2:00 PM

City Theater · Biddeford

$30 - $35

See details

23 mi

Santa Arrives by Fire Engine

Sun, Dec 13 · 2:00 PM

Cape Porpoise Kitchen · Kennebunkport

Free

See details

24 mi

Sparkling at 90: A Historic Holiday Soiree at the Nathanial Lord Thompson House

Sun, Dec 13 · 2:00 PM

Brick Store Museum · Kennebunk

$90

See details

24 mi

Christmas on The Farm with Santa and Mrs. Claus

Sun, Dec 13 · 1:00 PM

River Winds Farm & Estate · Kennebunk

See details

24 mi

Christmas on The Farm with Santa and Mrs. Claus

Sun, Dec 13 · 2:30 PM

River Winds Farm & Estate · Kennebunk

See details

0.7 mi

Home Free: Coming Home For The Holidays

Sun, Dec 13 · 7:30 PM

State Theatre · Portland

$35–$55

See details

0.8 mi

Lúnasa: An Irish Solstice Celebration (2 nights)

Mon, Dec 14 · 8:00 PM

One Longfellow Square · Portland

$40 advance / $45 day of show

See details

0.7 mi

Third Thursday: December Lights

Thu, Dec 17 · 10:00 AM

Portland Museum of Art · Portland

Free

See details

0.5 mi

Mr. Dickens and his Carol

Thu, Dec 17 · 5:00 PM

Victoria Mansion · Portland

Members $20 / Non-members $25

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Fri, Dec 18 · 2:00 PM

Merrill Auditorium · Portland

$28–$101

See details

24 mi

Holiday Open House

Fri, Dec 18 · 4:00 PM

Brick Store Museum · Kennebunk

Free

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Fri, Dec 18 · 7:00 PM

Merrill Auditorium · Portland

$28–$101

See details

15 mi

A Christmas Story: The Musical (Dec 18)

Fri, Dec 18 · 7:30 PM

City Theater · Biddeford

$30 - $35

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sat, Dec 19 · 2:00 PM

Merrill Auditorium · Portland

$28–$101

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sat, Dec 19 · 7:00 PM

Merrill Auditorium · Portland

$28–$101

See details

0.8 mi

Julia Haven Holiday Concert

Sat, Dec 19 · 8:00 PM

One Longfellow Square · Portland

$30 advance / $35 day of show

See details

15 mi

A Christmas Story: The Musical (Dec 19)

Sat, Dec 19 · 7:30 PM

City Theater · Biddeford

$30 - $35

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sun, Dec 20 · 1:00 PM

Merrill Auditorium · Portland

$28–$101

See details

0.2 mi

Portland Symphony Orchestra – Magic of Christmas

Sun, Dec 20 · 5:00 PM

Merrill Auditorium · Portland

$28–$101

See details

0.8 mi

A Havana New Year's Eve Bash with Primo Cubano!

Thu, Dec 31 · 9:00 PM

One Longfellow Square · Portland

$30 advance / $40 day of show

See details

15 mi

Lincoln's NYE Celebration!

Thu, Dec 31 · 9:00 PM

The Lincoln Hotel · Biddeford

$50-71

See details

24 mi

Rock the Boat: New Year's Eve at The Boathouse

Thu, Dec 31 · 9:00 PM

The Boathouse Waterfront Hotel & Restaurant · Kennebunkport

$33.85 (Eventbrite, with fees)

See details

12 mi

Special Olympics Maine Lobster Dip

Fri, Jan 1 · 10:00 AM

The Brunswick · Old Orchard Beach

See details