October 2026 Fairs & Festivals in Connecticut
49 events happening across Connecticut in October 2026.
Wethersfield Fall Thursday Farmers Market
Wethersfield Fall Thursday Farmers Market will be held on October 1st, 2026.
5(1)Harwinton Fair
An early-October Litchfield Hills fair — woodsmen shows, antique tractors, and a midway.
Portland Agricultural Fair
A River Valley October fair — livestock, tractor pulls, and farm competitions.
4.2(51)Southington Apple Harvest Festival
A two-weekend town-green festival — apple fritters, a carnival, a parade, and fireworks.
4.3(440)Berlin Craft Fair
Berlin Craft Fair will be held on October 3, 2026.
4.5(233)Bethel Autumn Craft Festival
Bethel Autumn Craft Festival will be held on October 3rd, 2026.
Litchfield Autumn Farmers Farmers Market
Litchfield Autumn Farmers Farmers Market will be held on October 3rd, 2026.
Madison Pride Fest
Madison Pride Fest will be held on October 3, 2026.
4.2(344)North Branford Fall Craft Fair
North Branford Fall Craft Fair will be held on October 3, 2026.
4.2(1098)Norwich Fall Marketplace
Norwich Fall Marketplace will be held on October 3, 2026.
4.8(830)Old Saybrook Arts and Crafts Festival
Old Saybrook Arts and Crafts Festival will be held on October 3-4, 2026.
5(5)The Old Wethersfield Arts and Crafts Fair
The Old Wethersfield Arts and Crafts Fair will be held on October 3rd, 2026.
Tony Inzero Autumn Outdoor Farmers Market
Tony Inzero Autumn Outdoor Farmers Market will be held on October 3rd, 2026.
Windsor Fall Festival
Windsor Fall Festival will be held on October 3-4, 2026.
Chowdafest
A New England chowder cook-off — taste, vote, and crown the best chowder for charity.
The Head of the Riverfront Regatta
The Head of the Riverfront Regatta will be held on October 4, 2026.
4.7(910)Wethersfield Autumn Farmers Market
Wethersfield Autumn Farmers Market will be held on October 8th, 2026.
Riverton Fair
The season-ending October country fair — oxen draws, woodsmen events, and home cooking.
4.5(14)Downtown Southington Apple Harvest Festival
Downtown Southington Apple Harvest Festival will be held on October 9-11, 2026.
How Bazaar The Makers Classic
The How Bazaar - The MakerÆs Classic will be held on October 9th, 2026.
Connecticut Garlic & Harvest Festival
A garlic-lover’s harvest festival in Bethlehem — garlic food, seed garlic, and cooking demos.
Browns Harvest Fall Festival
Brown’s Harvest Fall Festival will be held on October 10-11, 2026.
Connecticut Garlic and Harvest Festival
Connecticut Garlic and Harvest Festival will be held on October 10-11, 2026.
4.8(38)Gaylordsville Columbus Day Arts and Fine Crafts Show
Gaylordsville Columbus Day Arts and Fine Crafts Show will be held on October 10-12, 2026.
4.6(12)Greenwich Fall Art Festival
Greenwich Fall Art Festival will be held on October 10-11, 2026.
4.6(654)Greenwich Outdoor Crafts Festival
Greenwich Outdoor Crafts Festival will be held on October 10-11, 2026.
Litchfield Autumn Outdoor Farmers Market
Litchfield Autumn Outdoor Farmers Market will be held on October 10th, 2026.
4.6(24)Manchester Fall Pop-up Market
Manchester Fall Pop-up Market will be held on October 10-11, 2026.
Tony Inzero Autumn Farmers Market
Tony Inzero Autumn Farmers Market will be held on October 10th, 2026.
4.6(698)Wethersfield Craft Fair
Wethersfield Craft Fair will be held on October 10, 2026.
4.4(170)Danbury Pets in the Park
Danbury Pets in the Park will be held on October 11, 2026.
Glastonbury Apple Harvest & Music Festival
A riverside fall festival — apple treats, a carnival, craft vendors, and live music.
Gaylordsville Columbus Day Weekend Arts and Fine Crafts Show
Gaylordsville Columbus Day Weekend Arts and Fine Crafts Show will be held on October 16-18, 2026.
3(2)Blessing Pantry Fall Fair
Blessing Pantry Fall Fair will be held on October 17, 2026.
Browns Fall Outdoor Festival
Brown’s Fall Outdoor Festival will be held on October 17-18, 2026.
4(4)Connecticut Food Truck and Wine Festival
Connecticut Food Truck and Wine Festival will be held on October 17-18, 2026.
Litchfield Autumn Saturday Farmers Market
Litchfield Autumn Saturday Farmers Market will be held on October 17th, 2026.
Milford Fall Artisan Market
Milford Fall Artisan Market will be held on October 17-18, 2026.
5(1)Newtown Fall Arts and Craft Fair
Newtown Fall Arts and Craft Fair will be held on October 17, 2026.
Ridgefield Fall Arts Festival
Ridgefield Fall Arts Festival will be held on October 17-18, 2026.
4.5(230)Woodstock Fine Arts and Craft Festival
Woodstock Fine Arts and Craft Festival will be held on October 17-18, 2026.
Mystic Health and Wellness Expo
Mystic Health and Wellness Expo will be held on October 18, 2026.
4.3(37)New London Boo Bash
New London Boo Bash will be held on October 18th, 2026.
Hamden Boo Tique Monster Bash Market
Event will be held on October 24-25, 2026.
4.2(5)Unionville Fall Craft Fair
Unionville Fall Craft Fair will be held on October 24, 2026.
4.1(109)Windsor Fall Outdoor Festival
Windsor Fall Outdoor Festival will be held on October 24-25, 2026.
4.4(105)Hartford Howloween Event
Hartford Howloween Event will be held on October 28, 2026.
Browns Fall Festival 1
Brown’s Fall Festival will be held on October 31 - November 1, 2026.
4.5(2239)Hartford Fall Home Show
Hartford Fall Home Show will be held on October 31 - November 1, 2026.