October 3, 2026
RiverFest
Young's Field and Downtown New Milford • 11:00 AM–after dark
This free Housatonic River celebration is a convenient regional outing from Bogus Hill, with live music, food trucks, children’s activities, arts and crafts, a color fun run, evening River Lights, and fireworks. It offers an easy full-day destination for families, couples, and residents wanting to enjoy New Milford’s riverfront.
View event details →
September 5–October 4, 2026
24th Annual Housatonic Heritage Walks
Sites throughout the Housatonic River and Litchfield County region
Residents near Kent can choose from guided walks, talks, and heritage activities highlighting the Housatonic region’s landscapes, history, and cultural resources. The program is especially appealing in early October, when fall color and comfortable hiking weather make nearby towns and scenic sites enjoyable without requiring a long trip.
View event details →
October 3, 2026
Family Nature Day
White Memorial Conservation Center, Litchfield • 9:00 AM–3:00 PM
White Memorial’s annual Family Nature Day provides a family-friendly way for Bogus Hill residents to spend a fall Saturday outdoors, with nature-focused activities and educational experiences for children and adults. Litchfield is a reasonable regional drive from Kent, making this a strong seasonal option when local calendars are limited.
View event details →
October 16–November 21, 2026
Fall Juried Show
Kent Art Association, 21 South Main Street, Kent • Thursday–Saturday 1:00–5:00 PM; Sunday 12:00–4:00 PM
Located in central Kent and close to Bogus Hill, this juried exhibition offers an easy local cultural outing during October. Visitors can combine a gallery visit with shopping, coffee, or dinner downtown, making it a relaxed way to support regional artists and enjoy Kent’s fall atmosphere.
View event details →
October 25, 2026
50th Annual Kent Pumpkin Run
Kent Green Shopping Center and roads through Kent • Kids Fun Run 10:30 AM; 5-mile race 11:00 AM
Kent’s signature autumn community event is especially convenient for Bogus Hill residents, offering scenic running, a costume contest, age-group awards, and a kids’ fun run. Even nonparticipants can enjoy the festive crowd, cheer for runners, then spend the afternoon visiting Kent’s restaurants, shops, and galleries.
View event details →