Spectacular Fall Events and Activities

dheerajdagar • September 7, 2021
A white church in the middle of a forest with mountains in the background and New England fall foliage all around.

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.


Grab a picnic and enjoy five acres of glorious foliage around the picnic tables throughout the property. Nearby is Norbrook Farm Brewery with disc golf and a mountain bike trail surrounded by forests.

  • A round stone picnic table and benches under a tree with red leaves.

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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.

  • A group of people are riding bicycles down a dirt road in the woods.

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Tour-de-Forest


The Tour-de-Forest is a 13-mile ride with an even mix of gravel and paved roads. All roads are very rural, scenic and, for the most part, very lightly traveled. Half of the Tour-de-Forest is on a private gravel road with no cars allowed. Bikes with extremely thin tires are not encouraged. A hybrid or mountain bike is best. Free refreshments (both before and after) and a cash bar will be available at the curling club after the ride. Registration starts at 8 am. The Icebox Gravel starts at 9:30 am. The Tour-de-Forest starts at 10 am. The event is on Saturday 10/18/2025. Registration is $50 for adults, $25 for teens, and 12 & under is free.  All proceeds go to supporting the Norfolk Rails to Trails and Great Mountain Forest. 


Haystack Mountain Challenge


Looking for a fun fall challenge? On Sunday, October 5, 2025 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!

  • A lake surrounded by trees on a sunny day with fall foliage colors

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Haystack Book Talks

  • A beautiful wood-paneled library with arched ceilings, large windows, and lots of books

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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 October 3-5, 2025. This year’s festival requires advance registration for in-person attendees (limited number of seats).

Black Bear Americana Music Fest


This exciting music outdoor festival, held at the Harwinton Fairgrounds from August 22-24, 2025 includes 3 days of music by more than over 50 bands on four stages, covering rock, blues, folk, and bluegrass. With food trucks, and family-friendly activities, it’s the perfect way to close out summer in Connecticut.

  • A group of people are playing instruments on a stage.

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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!