Annual Events

Fireworks throughout the summer!

Craft EXPO, Guilford
July 16-18, 2027
www.guilfordartcenter.org

Orange Volunteer Firemen’s Carnival, Orange
July
www.orangevfd.com 

Annual Potato and Corn Festival, North Branford
August 6-8, 2027
www.nbpotatofest.com

Annual Shoreline Jewish Festival, Guilford
August
www.shorelinejewishfestival.com

Elm Shakespeare Company in the Park
Late August
www.elmshakespeare.org

Black Wall Street
Mid-August
www.bwsfestival.com

Milford Oyster Festival, Milford
Mid-August
www.milfordoysterfestival.com

Fair on the Half Shell
Mid-August
downtownmilfordct.com

Odyssey: A Greek Festival, Orange
Labor Day Weekend
www.saintbarbara.org

Annual Faxon Law New Haven Road Race, New Haven
September 6, 2027
www.newhavenroadrace.org

North Haven Fair, North Haven
September
www.northhaven-fair.com

East Haven Fall Festival
September
www.ehfallfestival.com/

New Haven Cocktail Week
September
www.newhavencocktailweek.com

The Guilford Fair
September 17-19, 2027
www.guilfordfair.org

Closer to Free Ride
September
www.rideclosertofree.org

New Haven Grand Prix & Apizza Feast
September
www.newhavengp.com

The Durham Fair
September 24-27, 2026
durhamfair.com

CT Folk Fest & Green Expo
September
www.ctfolk.org

Orange Country Fair
September 19 & 20, 2027
www.orangectfair.com

Celebrate Wallingford
October
wallingfordcenterinc.com

New Haven Chalk Art Festival
October
theshopsatyale.com

New Haven Dragon Boat Festival
October
www.canaldock.org

Downtown Milford Business Association Annual Wine Trail
October
downtownmilfordct.com

Bethany Harvest Festival
October
facebook.com/BethanyHarvestFestival

Fall Festival at The Big Red Barn
Open daily through November 1
bishopsorchards.com

New Haven Restaurant Week
November 1-14, 2026
Website

Trail of Terror in Wallingford
Through October (weekends)
trailofterror.com

Fall Festival at The Big Red Barn
Open daily through November 3
bishopsorchards.com

The Orchards Trials
Through October (weekends)
lymanorchards.com

New Haven Ghost Tour
Ongoing Friday & Saturday
ghostsofnewhaven.com

Free Family Fun Day
October
shubert.com

In Search of Sasquatch: CT Bigfoot Halloween Adventure
Weekends in October
thehauntedtrolley.com

Pumpkin Patch at the Shore Line Trolley Museum
Weekends in October
Website

Annual Christmas Exhibition at the McGivney Center
November-January
michaelmcgivneycenter.org

Holiday Expo at Guilford Art Center
November 14, 2026-January 11, 2027
guilfordartcenter.org

Holiday Worth Tasting Walking Tours
December 12, 2026
worthtasting.co

Fantasy of Lights
Canceled in 2026 due to storm damage.
goodwillsne.org

Festival of Silver Lights at Hubbard Park
Thanksgiving-January 1
More info

Holiday Events & Promotions at The Shops at Yale
November-December
theshopsatyale.com

Meet Santa at the Shore Line Trolley Museum
Thanksgiving-Christmas (weekends)
shorelinetrolley.org

Annual Orange CT Lighted Tractor Parade
December
orangetractorparade.com

Breakfast with Santa at the Shore Line Trolley Museum
December
shorelinetrolley.org

Firelight Festival at the Henry Whitfield State Museum
December
Website

Annual JCC Craft & Gift Fair
December
jewishnewhaven.org

Christmas in the Mansion
December
lauraltonhall.org

Eagle Watches on the Connecticut River from the Audubon Shop, Madison
February
www.theaudubonshop.com

St. Patrick’s Day Parade, Milford
March 14, 2026
Details

New Haven Restaurant Week
March 15-28, 2026
Website

St. Patrick’s Day Parade, New Haven
March 15, 2026
www.stpatricksdayparade.org

St Patrick’s Day Parade, Meriden
March 28, 2026
Website