Spectacular Fall Events and Activities

Stunning fall foliage and crisp, cool weather make fall a wonderful time to visit Connecticut’s northwest corner. With thousands of acres of preserved land and 3 state parks, Norfolk offers many fun activities for celebrating autumn’s incredible beauty.  Below are some of the exciting upcoming fall activities in Norfolk and the surrounding area that will make your autumn visit a memorable one.

Plus, there’s always our Craft Brewery Guide or Hiking & Picnic packages to round out your weekend!

Spectacular Fall Foliage Drives

Head to the northwestern corner of Connecticut for a memorable fall foliage drive featuring historic New England architecture, covered bridges and scenic farmland. We recommend Loop 2!

Only Mother Nature knows for sure, but leaves in the northwestern corner typically start changing in late September and get more and more vibrant through the end of October.

There’s no better place to view fall foliage than from the top of Norfolk’s Haystack Mountain, one of Connecticut’s highest peaks. The historic stone tower provides 360 degree views of peaks in 3 states: New York, Massachusetts and Vermont. Hikers can either take a longer trail with a gradual incline from the park entrance (~1.5 miles) or drive up to a small parking area and hike just ½ mile up to the tower. You’ll be rewarded with a stunning view no matter which hike you choose.

Haystack Mountain Challenge

Looking for a fun fall challenge? On Saturday, September 10, 2022 the Norfolk Land Trust will hold its Annual Haystack Mountain Challenge. Choose either the 5k route, a challenging and scenic race through picturesque Barbour Woods, or the 10k route which continues up Haystack Mountain. Or, for the extremely adventurous, run the half marathon!

Haystack Book Talks

Tucked away in the beautiful hills of northwestern Connecticut, Norfolk provides an intimate setting for this literary festival. Haystack Book Talks will facilitate engaging conversations with writers and thinkers from September 30 – October 2, 2022. This year’s festival requires advance registration for in-person attendees (limited number of seats).  The event kicks off with a discussion with Robert Jones, Jr., bestselling author of the critically acclaimed novel The Prophets, a singular and stunning debut novel about the forbidden union between two enslaved young men on a Deep South plantation, the refuge they find in each other, and a betrayal that threatens their existence.

Tour de Forest

This 13-mile recreational bicycle ride through Norfolk’s pristine Great Mountain Forest will be held on Sunday, October 9. The ride includes a mix of dirt and paved roads (hybrid or mountain bikes are recommended). Participants are encouraged to stop at 8 informational stops to learn about the forest and the railroad history. Refreshments will be available at the Norfolk Curling Club after the ride, along with explanations and demonstrations of curling.


Black Bear Americana Music Fest

This exciting music outdoor festival, held at the Goshen Fairgrounds from October 7-9, 2022 includes 3 days of music by more than 35 performers on 4 stages.  Hear favorite Folk, Indie, Soul, American Roots and Blues artists including favorites such as Rusted Root’s Michael Glabicki, The Slambovian Circus of Dreams, Adam Ezra Group, and Atlas Gray.



Berkshire Botanical Garden

A showcase of horticulture and garden design and a “museum of living things,” Berkshire Botanical Garden, in nearby Stockbridge, MA, features more than 20 acres of display areas that are educational, functional, and ornamental, with collections emphasizing plants that are native to the Northeast. Among the oldest in the region, their spectacular gardens have evolved and expanded over the years in breadth and variety, with its newest, “Lucy’s Garden” featuring topiary animals and other ‘live’ sculptures.

After your day of exploring, come back to the inn and relax by the massive fireplace in our Great Room or book one of our fireplace suites.


Fall reservations go quickly so book your Manor House Inn visit today!