Through February 1
The Spirit of Christmas at the McGivney Center
Through January 11
Holiday Expo at Guilford Art Center
November 21-December 31
Fantasy of Lights
November 21
NHSO: Holiday Extravaganza
November 25
Holiday Trivia Night
November 28-January 1
Festival of Silver Lights at Hubbard Park
November 28-December 21
Holiday Events & Promotions at The Shops at Yale
November 28 & 29
Holidaze… by Cirque du Soleil
November 28-December 21 (weekends)
Next Stop: Santa
November 29
Annual Bonfire & Tree Lighting at the Madison Beach Hotel
November 29
Branford Tree Lighting & Parade
November 29
Christmas Tree Lighting Ceremony
November 29
East Haven Chamber Annual Tree Lighting on the Green
November 29
Milford Holiday Pop-Up – Small Business Saturday Edition
November 29 & 30
Miracle on 34th Street – The Musical
Saturdays, November 29, December 13 & 20
The Shops at Yale: Ice Carving Competition & A Capella Concert
December 3-14
Scrooge and Marley at the Legacy Theatre
December 5
Guilford Tree Lighting
December 5
Holiday Stroll (Wallingford)
December 5
North Branford Annual Tree Lighting & Festivities
December 5-21
Pantochino: Welcome to Santa Claus
December 5
The 23rd Annual Lamplight Stroll in Milford
December 5
Walnut Beach Tree Lighting (Milford)
December 6
Annual Orange CT Lighted Tractor Parade
December 6, 13, & 20
Breakfast with Santa at the Shore Line Trolley Museum
December 6
Firelight Festival at the Henry Whitfield State Museum
December 6
Wallingford Seasons of Celebration
December 6-21 (weekends)
Holiday Magic at Lyman Orchards
December 7
Annual JCC Craft & Gift Fair
December 7
Cheshire Annual Winter Wonderland
December 7
Christmas in Clinton
December 7
Christmas in the Mansion
December 7
North Haven Tree Lighting & Santa’s Workshop
December 12-14
New Haven Ballet presents The Nutcracker
December 13
Holiday Worth Tasting Walking Tours
December 14
Hanukkah Menorah Lighting Ceremony
December 15
Engelbert Humperdinck – A Winter World of Love at the Shubert
December 16
North Haven Menorah Lighting
December 18
Sip & Shop in Downtown Milford
December 19
Ireland With Michael LIVE Holiday Show
December 19
NHSO Holiday Extravaganza: Joy to the World!
December 29
Fire & Ice Chanukah
December 30
Branford Chanukah Concert & Menorah Lighting
December 30
Menorah Lighting & Concert
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
New Haven Spring Restaurant Week
April 6-11, 2025
www.infonewhaven.com/dining/nhrwinfo/
Cherry Blossom Festival, New Haven
The 2025 festival is canceled due to a rainy forecast. We’ll see you next year on April 12, 2026
www.historicwoostersquare.org
Annual Meriden Daffodil Festival
May 3 & 4, 2025
www.daffodilfest.com
Freddy Fixer Parade, New Haven
June 1, 2025
www.elmcityfreddyfixerparade.com
Pirate’s Day, Milford
June 8, 2025
www.downtownmilfordct.com
International Festival of Arts & Ideas, New Haven
June 14-28, 2025
www.artidea.org
Connecticut Open House Day
June 7, 2025
www.ctvisit.com
Branford Festival
June 13-15, 2025
www.branfordfestival.com
Branford Road Race
June 15, 2025
www.branfordroadrace.com
Fireworks throughout the summer!
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
Annual Shoreline Jewish Festival, Guilford
August 10, 2025
www.shorelinejewishfestival.com
Elm Shakespeare Company in the Park
August 13-31 7:30 p.m, No Mondays
www.elmshakespeare.org
Black Wall Street
August 16, 2025
www.bwsfestival.com
Milford Oyster Festival, Milford
August 15 & 16, 2025
www.milfordoysterfestival.com
Fair on the Half Shell
August 16, 2025
Website (temporary event listing)
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
September 4-7, 2025
www.northhaven-fair.com
East Haven Fall Festival
September 5-7, 2025
www.facebook.com/EHFallFest
Closer to Free Ride
September 6, 2025
www.rideclosertofree.org
CT Folk Fest & Green Expo
September 6, 2025
www.ctfolk.org
New Haven Cocktail Week
September 7-13, 2025
www.newhavencocktailweek.com
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
September 20 & 21, 2025
www.orangectfair.com
Odyssey: A Greek Festival, Orange
August 29-September 1, 2025
saintbarbara.org
Annual Faxon Law New Haven Road Race, New Haven
September 1, 2025
newhavenroadrace.org
North Haven Fair, North Haven
September 4-7, 2025
northhaven-fair.com
East Haven Fall Festival
September 5-7, 2025
facebook.com/EHFallFest
CT Folk Fest & Green Expo
September 6, 2025
ctfolk.org
Closer to Free Ride
September 6, 2025
rideclosertofree.org
New Haven Cocktail Week
September 7-13, 2025
newhavencocktailweek.com
New Haven Grand Prix & Apizza Feast
September 12, 2025
newhavengp.com
The Guilford Fair
September 19-21, 2025
guilfordfair.org
Orange Country Fair
September 20 & 21, 2025
orangectfair.com
Celebrate Wallingford
October 4-5, 2025
wallingfordcenterinc.com
Downtown Milford Business Association Annual Wine Trail
October 4, 2025
downtownmilfordct.com
Bethany Harvest Festival
October 5, 2025
facebook.com/BethanyHarvestFestival
New Haven Chalk Art Festival
October 11, 2025
theshopsatyale.com
Trail of Terror in Wallingford
Through October (weekends)
trailofterror.com
Fall Festival at The Big Red Barn
Open daily through November 1
bishopsorchards.com
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
Through February 1
The Spirit of Christmas at the McGivney Center
Through January 11
Holiday Expo at Guilford Art Center
November 21-December 31
Fantasy of Lights
November 21
NHSO: Holiday Extravaganza
November 25
Holiday Trivia Night
November 28-January 1
Festival of Silver Lights at Hubbard Park
November 28-December 21
Holiday Events & Promotions at The Shops at Yale
November 28 & 29
Holidaze… by Cirque du Soleil
November 28-December 21 (weekends)
Next Stop: Santa
November 29
Annual Bonfire & Tree Lighting at the Madison Beach Hotel
November 29
Branford Tree Lighting & Parade
November 29
Christmas Tree Lighting Ceremony
November 29
East Haven Chamber Annual Tree Lighting on the Green
November 29
Milford Holiday Pop-Up – Small Business Saturday Edition
November 29 & 30
Miracle on 34th Street – The Musical
Saturdays, November 29, December 13 & 20
The Shops at Yale: Ice Carving Competition & A Capella Concert
December 3-14
Scrooge and Marley at the Legacy Theatre
December 5
Guilford Tree Lighting
December 5
Holiday Stroll (Wallingford)
December 5
North Branford Annual Tree Lighting & Festivities
December 5-21
Pantochino: Welcome to Santa Claus
December 5
The 23rd Annual Lamplight Stroll in Milford
December 5
Walnut Beach Tree Lighting (Milford)
December 6
Annual Orange CT Lighted Tractor Parade
December 6, 13, & 20
Breakfast with Santa at the Shore Line Trolley Museum
December 6
Firelight Festival at the Henry Whitfield State Museum
December 6
Wallingford Seasons of Celebration
December 6-21 (weekends)
Holiday Magic at Lyman Orchards
December 7
Annual JCC Craft & Gift Fair
December 7
Cheshire Annual Winter Wonderland
December 7
Christmas in Clinton
December 7
Christmas in the Mansion
December 7
North Haven Tree Lighting & Santa’s Workshop
December 12-14
New Haven Ballet presents The Nutcracker
December 13
Holiday Worth Tasting Walking Tours
December 14
Hanukkah Menorah Lighting Ceremony
December 15
Engelbert Humperdinck – A Winter World of Love at the Shubert
December 16
North Haven Menorah Lighting
December 18
Sip & Shop in Downtown Milford
December 19
Ireland With Michael LIVE Holiday Show
December 19
NHSO Holiday Extravaganza: Joy to the World!
December 29
Fire & Ice Chanukah
December 30
Branford Chanukah Concert & Menorah Lighting
December 30
Menorah Lighting & Concert
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
New Haven Spring Restaurant Week
April 6-11, 2025
www.infonewhaven.com/dining/nhrwinfo/
Cherry Blossom Festival, New Haven
April 6, 2025 – The 2025 festival is canceled due to a rainy forecast. We’ll see you next year on April 12, 2026
www.historicwoostersquare.org
Annual Meriden Daffodil Festival
May 3 & 4, 2025
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
June 14-28, 2025
www.artidea.org
Connecticut Open House Day
June 7, 2025
www.ctvisit.com
Branford Festival
June 13-15, 2025
www.branfordfestival.com
Branford Road Race
June 15, 2025
www.branfordroadrace.com
Fireworks throughout the summer!
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
Odyssey: A Greek Festival, Orange
August 29-September 1, 2025
saintbarbara.org
Annual Faxon Law New Haven Road Race, New Haven
September 1, 2025
newhavenroadrace.org
North Haven Fair, North Haven
September 4-7, 2025
northhaven-fair.com
East Haven Fall Festival
September 5-7, 2025
facebook.com/EHFallFest
CT Folk Fest & Green Expo
September 6, 2025
ctfolk.org
Closer to Free Ride
September 6, 2025
rideclosertofree.org
New Haven Cocktail Week
September 7-13, 2025
newhavencocktailweek.com
New Haven Grand Prix & Apizza Feast
September 12, 2025
newhavengp.com
The Guilford Fair
September 19-21, 2025
guilfordfair.org
Orange Country Fair
September 20 & 21, 2025
orangectfair.com
Celebrate Wallingford
October 4-5, 2025
wallingfordcenterinc.com
Downtown Milford Business Association Annual Wine Trail
October 4, 2025
downtownmilfordct.com
Bethany Harvest Festival
October 5, 2025
facebook.com/BethanyHarvestFestival
New Haven Chalk Art Festival
October 11, 2025
theshopsatyale.com
Trail of Terror in Wallingford
Through October (weekends)
trailofterror.com
Fall Festival at The Big Red Barn
Open daily through November 1
bishopsorchards.com
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