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 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, New Haven
March 16, 2025
www.stpatricksdayparade.org
New Haven Spring Restaurant Week
Mid April
www.infonewhaven.com/dining/nhrwinfo/
Cherry Blossom Festival, New Haven
April 6, 2025
www.historicwoostersquare.org
Annual Meriden Daffodil Festival
Early May
www.daffodilfest.com
Freddy Fixer Parade, New Haven
Early June
www.elmcityfreddyfixerparade.com
Pirate’s Day, Milford
Early June
www.downtownmilfordct.com
International Festival of Arts & Ideas, New Haven
Mid-June
www.artidea.org
Connecticut Open House Day
Early June
www.ctvisit.com
Branford Festival
June 13-15, 2025
www.branfordfestival.com
Branford Road Race
June 15, 2024
www.branfordroadrace.com
Annual Shoreline Jewish Festival, Guilford
Mid July
www.shorelinejewishfestival.com
Craft EXPO, Guilford
Mid July
www.guilfordartcenter.org
Orange Volunteer Firemen’s Carnival, Orange
Early August
www.orangevfd.com
Annual Potato and Corn Festival, North Branford
Early August
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 29-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
September 12, 2025
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
Early October
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 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, New Haven
March 16, 2025
www.stpatricksdayparade.org
New Haven Spring Restaurant Week
Mid April
www.infonewhaven.com/dining/nhrwinfo/
Cherry Blossom Festival, New Haven
April 6, 2025
www.historicwoostersquare.org
Annual Meriden Daffodil Festival
Early May
www.daffodilfest.com
Freddy Fixer Parade, New Haven
Early June
www.elmcityfreddyfixerparade.com
Pirate’s Day, Milford
Early June
www.downtownmilfordct.com
International Festival of Arts & Ideas, New Haven
Mid-June
www.artidea.org
Connecticut Open House Day
EarlyJune
www.ctvisit.com
Branford Festival
June 13-15, 2025
www.branfordfestival.com
Branford Road Race
June 15, 2024
www.branfordroadrace.com
Annual Shoreline Jewish Festival, Guilford
Mid July
www.shorelinejewishfestival.com
Craft EXPO, Guilford
Mid July
www.guilfordartcenter.org
Orange Volunteer Firemen’s Carnival, Orange
Early August
www.orangevfd.com
Annual Potato and Corn Festival, North Branford
Early August
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
Early October
www.infonewhaven.com/dining/nhrwinfo/