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Connecticut Fairs & Festivals in September 2026

48 upcoming events. Everything on the calendar for September 2026.

Showing 18 of 48 events

Fair illustration
SEP
17
In 11 days

Berlin Fair 2026 — Sep 17–20 in Berlin, CT

Thu, Sep 17, 2026 - Sun, Sep 20, 2026
Berlin Fairgrounds, Berlin, CT
Outdoor
FairAgricultural Fair
Fair illustration
SEP
17
In 11 days

Four Town Fair 2026

Thu, Sep 17, 2026 - Sun, Sep 20, 2026
Four Town Fairgrounds, Somers, CT
Medium Outdoor
FairAgricultural Fair
Fair illustration
SEP
18
In 12 days

Guilford Fair 2026 — Sep 18–20 in Guilford, CT

Fri, Sep 18, 2026 - Sun, Sep 20, 2026
Guilford Fairgrounds, Guilford, CT
Outdoor
FairAgricultural Fair
Festival illustration
SEP
18
In 12 days

Cheshire-Prospect Fall Festival 2026

Fri, Sep 18, 2026 - Sat, Sep 19, 2026
Bartlem Park, Cheshire, CT
Medium Outdoor
FestivalCraft FairCommunity Event
Photo of Greater Waterbury Puerto Rican Parade and Festival 2026 event
In 12 days

Greater Waterbury Puerto Rican Parade and Festival 2026

Fri, Sep 18, 2026 - Sat, Sep 19, 2026
Library Park, Waterbury, CT
Large Outdoor
FestivalCulturalParade
Agricultural Fair illustration
SEP
19
In 13 days

Orange Country Fair 2026

Sat, Sep 19, 2026 - Sun, Sep 20, 2026
Orange Fairgrounds, Orange, CT
Medium
Agricultural Fair
Photo of Olde Mistick Village Garlic Festival 2026 event
In 13 days

Olde Mistick Village Garlic Festival 2026

Sat, Sep 19, 2026 - Sun, Sep 20, 2026
Olde Mistick Village, Mystic, CT
Medium Outdoor
FestivalFood FestivalCraft Fair
Photo of Bloomfield Food Truck Festival 2026 event
In 13 days

Bloomfield Food Truck Festival 2026

Sat, Sep 19, 2026 - Sun, Sep 20, 2026
Bloomfield Town Center, Bloomfield, CT
Small Outdoor
FestivalFood Festival
Craft Fair illustration
SEP
20
In 14 days

Seymour Pumpkin Festival 2026

Sun, Sep 20, 2026
French Memorial Park, Seymour, CT
Large Outdoor
Craft FairFestivalHarvest Festival
Photo of Shore Line Trolley Museum Pre-Holiday Store Sale event
In 14 days

Shore Line Trolley Museum Pre-Holiday Store Sale

Sun, Sep 20, 2026
Shore Line Trolley Museum, East Haven, CT
Small Mixed
FestivalHoliday Market
Boat Show illustration
SEP
24
In 18 days

Norwalk Boat Show 2026

Thu, Sep 24, 2026 - Sun, Sep 27, 2026
Norwalk Cove Marina, Norwalk, CT
Outdoor~10,000
Boat Show

Vendors (1)

Fair illustration
SEP
24
In 18 days

Durham Fair 2026

Thu, Sep 24, 2026 - Sun, Sep 27, 2026
Durham Fairgrounds, Durham, CT
Mixed
Fair
Photo of Milford Oktoberfest 2026 event
In 19 days

Milford Oktoberfest 2026

Fri, Sep 25, 2026 - Sat, Sep 26, 2026
Fowler Field, Milford, CT
$10
Outdoor
FestivalBeer FestivalMusic Festival
Festival illustration
SEP
25
In 19 days

Bristol Mum Festival 2026

Fri, Sep 25, 2026 - Sun, Sep 27, 2026
Memorial Boulevard, Bristol, Bristol, CT
Large Outdoor
FestivalCraft FairCommunity Event
Gun Show illustration
SEP
26
Expected in 20 days

Plainville Gun Show

Sat, Sep 26, 2026
VFW Madley Roberts Post #574, Plainville, CT
$10
Small Indoor
Gun Show
Photo of Stafford AppleFest 2026 event
In 20 days

Stafford AppleFest 2026

Sat, Sep 26, 2026
Downtown Stafford Springs, Stafford Springs, CT
Free
Outdoor
FestivalFood FestivalHarvest Festival
Photo of Celebrate Mansfield Festival 2026 event
In 20 days

Celebrate Mansfield Festival 2026

Sat, Sep 26, 2026 - Sun, Sep 27, 2026
Downtown Storrs Mansfield Town Square, Storrs, CT
Small Outdoor
FestivalCommunity Event
Festival illustration
SEP
27
In 21 days

Trumbull Arts Festival 2026

Sun, Sep 27, 2026
Town Hall Green, Trumbull, CT
Free
Outdoor
FestivalCraft FairArt Show

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