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Fairs & Festivals in Greater Portland & Casco Bay, Maine

25 upcoming events. Portland, South Portland and the towns around Casco Bay.

Showing 25 of 25 events

Photo of Portland Farmers Market - Monument Square (Wednesday) 2026 event
In 2 days

Portland Farmers Market - Monument Square (Wednesday) 2026

Next: Wed, Sep 23, 2026
Monument Square, Portland, ME
Farmers Market
Photo of Portland Farmers Market - Deering Oaks (Saturday) 2026 event
This weekend

Portland Farmers Market - Deering Oaks (Saturday) 2026

Next: Sat, Sep 26, 2026
Deering Oaks Park, Portland, ME
Farmers Market
Photo of Cumberland Fair 2026 event
This weekend

Cumberland Fair 2026

Sun, Sep 27, 2026 - Sat, Oct 3, 2026
Cumberland County Fair, Cumberland Center, ME
Up to $15
Medium
Fair
Festival illustration
OCT
2
In 11 days

Freeport Fall Festival 2026 — Oct 2–4 in Freeport, ME

Fri, Oct 2, 2026 - Sun, Oct 4, 2026
Downtown, Freeport, ME
Festival
Photo of Old Port Makers Market event
In 12 days

Old Port Makers Market

Sat, Oct 3, 2026
Old Port Square, Portland, ME
Small Outdoor
Craft FairMarket
Craft Fair illustration
OCT
10
Expected in 19 days

Annual Columbus Weekend Arts & Craft Show

Sat, Oct 10, 2026 - Sun, Oct 11, 2026
Westbrook Community Center, Westbrook, ME
Small
Craft Fair

Vendors (1)

Maine Cardworks Inc logo
Market illustration
OCT
17
In 26 days

Standish Makers Market - October

Sat, Oct 17, 2026
Hometown Furnishing Co, Standish, ME
Outdoor
Market
Photo of Harvest on the Harbor 2026 event

Harvest on the Harbor 2026

Sat, Oct 24, 2026 - Mon, Oct 26, 2026
Portland Waterfront, Portland, ME
Outdoor
Food Festival
Craft Fair illustration
OCT
24
Tentative

SSMC Craft Show - Portland 2026

Sat, Oct 24, 2026 - Sun, Oct 25, 2026
Stevens Square Community Center, Portland, ME
Free
Small Indoor
Craft Fair
Photo of Portland Holiday Market event

Portland Holiday Market

Fri, Nov 6, 2026 - Sun, Nov 8, 2026
James A Banks Sr Portland Exposition Building, Portland, ME
Holiday Market
Craft Fair illustration
NOV
7
Tentative

SSMC Craft Show - South Portland 2026

Sat, Nov 7, 2026 - Sun, Nov 8, 2026
South Portland High School, South Portland, ME
Free
Small Indoor
Craft Fair
Photo of Kids Con New England event

Kids Con New England

Sat, Nov 14, 2026
DoubleTree by Hilton, South Portland, ME
Indoor
Comic Con
Craft Fair illustration
NOV
14

USM Craft Show - Fall

Sat, Nov 14, 2026 - Sun, Nov 15, 2026
University of Southern Maine - Gorham Campus, Gorham, ME
Indoor
Craft Fair
Art Show illustration
NOV
14
Tentative

Falmouth Open Studio Tour 2026

Sat, Nov 14, 2026
Various Studios (Falmouth), Falmouth, ME
Free
Small Indoor
Art ShowArt Walk
Makers Market illustration
NOV
21

Makers Market Christmas Arts & Craft Show 2026

Sat, Nov 21, 2026 - Sun, Nov 22, 2026
South Portland High School, South Portland, ME
Medium
Makers Market

Vendors (1)

Maine Cardworks Inc logo
Craft Fair illustration
NOV
27
Tentative

Scarborough High School Craft Show 2026

Fri, Nov 27, 2026 - Sat, Nov 28, 2026
Scarborough High School, Scarborough, ME
Free
Indoor
Craft FairHoliday Market
Craft Fair illustration
NOV
27

Bonny Eagle Craft Fair

Fri, Nov 27, 2026 - Sat, Nov 28, 2026
Bonny Eagle High School, Standish, ME
Indoor
Craft Fair
Craft Fair illustration
NOV
27
Tentative

SSMC Craft Show - Scarborough 2026

Fri, Nov 27, 2026 - Sat, Nov 28, 2026
Scarborough High School, Scarborough, ME
Free
Small Indoor
Craft Fair
Photo of Caravan Holiday Blitz at Allagash Brewing 2026 event

Caravan Holiday Blitz at Allagash Brewing 2026

Sat, Dec 5, 2026 - Sun, Dec 6, 2026
The Cellars at Allagash, Portland, ME
Small Mixed
Craft FairMarket
Craft Fair illustration
DEC
12
Tentative

Designing Women Portland 2026

Sat, Dec 12, 2026
Ocean Avenue Elementary School, Portland, ME
Small Indoor
Craft Fair
Festival illustration
MAR
6
Tentative

Projected from last year — not yet published by the organizer

Freeport Chocolate Festival 2027

Sat, Mar 6, 2027
Greater Freeport Chamber of Commerce, Freeport, ME
Medium
Festival
Festival illustration
JUN
19
Tentative

Windham Summerfest 2027

Sat, Jun 19, 2027
Windham High School, Windham, ME
FestivalCommunity EventCraft Fair
Festival illustration
JUL
16
Tentative

Yarmouth Clam Festival 2027

Fri, Jul 16, 2027 - Sun, Jul 18, 2027
Yarmouth Village (Main Street), Yarmouth, ME
FestivalFood Festival
Photo of Cumberland County Fair 2027 event
Tentative

Projected from last year — not yet published by the organizer

Cumberland County Fair 2027

Sun, Sep 26, 2027 - Sat, Oct 2, 2027
Cumberland County Fair, Cumberland Center, ME
Fair
Photo of Northeast Egg & Art Expo 2026 event
Ended

Northeast Egg & Art Expo 2026

Thu, Sep 17, 2026 - Sun, Sep 20, 2026
Best Western Merry Manor Inn, South Portland, ME
Small Indoor
Art ShowCraft Fair

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