Annual Events

Annual Shoreline Jewish Festival, Guilford
Mid July
www.shorelinejewishfestival.com

Craft EXPO, Guilford
July 18-20, 2025
www.guilfordartcenter.org

Orange Volunteer Firemen’s Carnival, Orange
July 31-August 3, 2025
www.orangevfd.com 

Annual Potato and Corn Festival, North Branford
August 1-3, 2025
www.nbpotatofest.com

Black Wall Street
Mid August
www.bwsfestival.com

Elm Shakespeare Company in the Park
Mid August 7:30 p.m, No Mondays
www.elmshakespeare.org

Milford Oyster Festival, Milford
August 15 & 16, 2025
www.milfordoysterfestival.com

Odyssey: A Greek Festival, Orange
August 28-September 1, 2025
www.saintbarbara.org

Annual Faxon Law New Haven Road Race, New Haven
September 1, 2025
www.newhavenroadrace.org

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

East Haven Fall Festival
Early September
www.facebook.com/EHFallFest

Closer to Free Ride
Early September
www.rideclosertofree.org

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

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

Evidence of Evil Haunted Attraction
Through October (weekends)
lymanorchards.com

New Haven Ghost Tour
Ongoing Friday & Saturday
ghostsofnewhaven.com

The Rocky Horror Picture Show
October
shubert.com

Free Family Fun Day
October
shubert.com

Haunted Trolley FINAL STOP: Murder on the Rails
Weekends in October
thehauntedtrolley.com

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

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

The Guilford Fair
September 19-21, 2025
www.guilfordfair.org

Orange Country Fair
Late September
www.orangectfair.com

The Durham Fair
September 25-28, 2025
www.durhamfair.com

Fall Bird Walks at Hammonasset Beach State Park, Madison
Saturdays, Mid September-Mid November
www.theaudubonshop.com

New Haven Fall Restaurant Week
November 2-7, 2025
www.infonewhaven.com/dining/nhrwinfo/

Through 12/16 (Saturdays) Holidays at the Big Red Barn at Bishop’s Orchards

11/1-1/7 Guilford Art Center Holiday Expo

11/9-2/2 Christmas in Africa at the McGivney Center

11/9-2/2 Away in a Manger: The Creation of Nativity Scenes at the McGivney Center

11/22-12/31 Fantasy of Lights at Lighthouse Point Park

11/24 Annual Craft Fair at the JCC

11/27 Festival of Silver Lights & Tree Lighting in Meriden

11/29-12/24 (weekends) Storytelling & Selfies with Santa & Mrs. Claus

11/29-12/22 (weekends) Ice Carving Competition & A Cappella Concert at The Shops at Yale

11/29 Milford Christmas Market & Tree Lighting 2024

11/30 Annual Branford Tree Lighting & Parade on the Green

11/30 East Haven Chamber Annual Tree Lighting on the Green

11/30 West Haven Christmas Tree Lighting on the Green

12/1 Trees in the Rigging at the Connecticut River Museum

12/4-15 A Christmas Carol at the Legacy Theatre

12/5 New Haven Tree Lighting on the Green

12/5-7 Holiday Village on the New Haven Green

12/6 Guilford Tree Lighting

12/6 Madison Holiday Tree Lighting

12/6-12/22 Dorothy’s Christmas in Oz at the MAC

12/6 Firelight Festival at Henry Whitfield House State Museum

12/6 Wallingford Holiday Stroll

12/6 North Branford Annual Tree Lighting & Festivities

12/7 Orange Holiday Festival with the Lighted Tractor Parade and Tree Lighting

12/7 Wallingford Seasons of Celebration

12/7 Worth Tasting Holiday Food Tour

12/8 North Haven Tree Lighting

12/8 Walnut Beach Tree Lighting

12/12 noon-8 p.m. Branford’s Shop, Sip & Stroll

12/12 5-8 p.m. Ladies Holiday Shopping Night Out in Madison

12/13-15 New Haven Ballet Presents the Nutcracker

12/14 Hamden Annual Silverbells

12/14 NHSO: Holiday Extravaganza

12/22 NHSO: Caroling, Caroling

12/25 New Haven Menorah Lighting on the Green

12/26 Kwanzaa Kinara Lighting

12/26 Light Up Orange – A Chanukah Celebration

12/29 Guilford Fire & Ice Chanukah

12/29 Menorah Parade & Milford Lighting

12/30 North Haven Menorah Lighting on the Green

12/30 West Haven Hanukkah Menorah Lighting Ceremony on the Green

12/30 Chanukah Concert at the Blackstone Library, Branford

1/1 Guilford Rotary Frosty 5k Run

TBA Grand Menorah Lighting and Celebration at the Stop & Shop in Hamden

CT Winter Wine Trail
January-March
www.ctwine.com

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

Walter Camp Weekend, New Haven
Mid March
www.waltercamp.org

St. Patrick’s Day Parade, Milford
March 15, 2025
Details

St. Patrick’s Day Parade, New Haven
March 16, 2025
www.stpatricksdayparade.org