Cheshire County Fairs & Festivals 2026
Cheshire County, New Hampshire. Listed here: 7 events, all ended for 2026.
EndedFreeSeasonalFamilyFood Festival
Keene Pumpkin Festival
Community pumpkin festival in downtown Keene, distinct from the Laconia event.
Sat, Oct 17Keene
EndedFreeFood FestivalFamily
Winchester Pickle Festival
28th annual pickle-themed street festival in Winchester, 10 am to 4 pm.
Sat, Sep 26Winchester
EndedFreeCulturalFamily
Keene Pride
Keene's free Sunday Pride festival, with 100+ vendors and a drag show in Central Square.
Sun, Sep 20Keene
EndedAgriculturalFamily
Cheshire Fair
Four-day Monadnock-region agricultural fair with free military admission daily.
2026 date not confirmedSwanzey
EndedMusicArtisan
Northlands Music & Arts Festival
Three-day, three-stage camping music festival at the Cheshire Fairgrounds.
Fri–Sun, Jun 19–21Swanzey
EndedArtisanCultural
Keene Art Walk
Ten-day visual arts walk across downtown Keene venues.
2026 date not confirmedKeene
EndedFreeSeasonalFamily
Keene Ice and Snow Festival
23rd annual free winter festival in downtown Keene.
Sat, Feb 7Keene