Traditional Fall Activities you won’t want to miss!

Visit an Orchard

Pick your own apples, or just pick up your favorites by the bag or bushel. Try some apple cider and cider donuts.

Happy Valley Orchard, 217 Quarry Road, Middlebury – map | website
Douglas Orchards, 1050 VT Rt. 74, Shoreham, VT – map | website
Woodman Hill Orchard, 175 Plank Road, Vergennes, VT – map | website
Windfall Orchard, 1491 VT Rt. 30, Cornwall, VT – map | website

Pick Your Own Pumpkin

Whether you want to make a pie, decorate for the fall, or carve a jack-o-lantern, a visit to a Vermont pumpkin patch is the perfect place to start! Pick your own to get the most from this seasonal tradition.

Happy Valley Orchard, 217 Quarry Road, Middlebury – map | website
Next Chapter Farm, 2571 Route 7 South, Middlebury –  map | website

Go Leaf Peeping

The fall foliage in Vermont is stunning, so take a drive and find your favorite vistas. Here’s a couple of suggested driving tours in Addison County, but just about anywhere you go, you’ll be able to see this spectacular show put on by Mother Nature.

Stroll the Robert Frost Interpretive Trail

Enjoy woods and fields and poetry! Frost’s poems are mounted along this easy 1.2 mile loop. The first 0.3 mile is along a wheelchair-accessible boardwalk.

Directions from Middlebury: travel south on Route 7 to where it intersects with Route 125. Travel east on Route 125 for 5.8 miles. The parking area is on the right.

Visit the Middlebury Farmers Market

Enjoy a wide selection of local food including fresh produce, locally raised meat and eggs, locally made cheese, and Vermont crafts at the Middlebury Farmers Market. Open Wednesdays & Saturdays, 9am-12:30pm

map | website

Visit the Stone Mill Outdoor Public Market

Every Saturday from 12-5pm the Stone Mill Public Market hosts farmers, artists, makers, and entrepreneurs on the outdoor deck. Lost Monarch Coffee will be pouring and the Slate Home, Dedalus Wine and Cheese, and the Vermont Book Shop spaces will be open for additional shopping.

map | website

Hike the TAM (Trail Around Middlebury)

Hike (or bike) around Middlebury! Choose a section or do the whole trail in a day!

maps | website

Go Ride A Bike!

Cycling is a great way to enjoy the crisp fall air and foliage! Bike rentals are available from Frog Hollow Bikes in Middlebury, or you can stay on a farm and try out recumbent trikes and tandem bikes at RAD-Innovations in Cornwall. Cruise the Champlain Bikeway along the lake, find a mountain bike trail on the Addison County Bike Club website, or visit the Moosalamoo National Recreation Area.

Drive-Thru Trick or Treating at the Spooktacular!

Middlebury Spooktacular

An annual tradition with a drive-thru twist for 2020 – a fun and safe Halloween activity!

A list of stops and a map will be available soon!

Shop Downtown Middlebury

Downtown Middlebury & The Marble Works Sidewalk Sales

Downtown Middlebury is open and ready to welcome you! Don’t miss the sidewalk sale October 10-12, which will include pop-ups throughout the weekend with live music, artisans, and lots more. 

Check out more outdoor recreation options here

Browse Middlebury’s shopping options here

Find Middlebury dining options here