What to do in the Fall in the Berkshires

No matter where I go, no place feels more like home than the Berkshires, and no time feels more magical there than the fall.

Between the foliage, the apple picking and the activities, it’s truly a glorious time to visit. If you’ve never been to the area before, I highly recommend an autumn visit for your first experience. Here are some of my favorite things to do during the fall in the Berkshires.

MOUNT GREYLOCK

We always enter on the Lanesborough side of the mountain off of Route 7, onto Rockwell Road, which takes you past the visitor’s center and on up to the summit (with plenty of places to stop for hikes and/or views along the way). Notch Road, from the North Adams side, will also take you up to the same spot. At the summit, you can park (for a small fee), hike, take in the views and enjoy a picnic or grab lunch at Bascom Lodge (be sure to check their hours first as they tend to close for the season in Mid-October). There’s also this helpful guide on drives and hikes to see the best foliage on Greylock.

ROUTE 7

We start in Lanesborough and usually turn around in Bennington, VT, which is roughly a 40 minute drive, but plan extra time to stop and take in the foliage as well as a stop in Williamstown

A FEW OF MY FAVORITE HIKING SPOTS IN THE AREA

APPLE PICKING

I like going to either Lakeview Orchard or Bartlett’s

Cider Donuts 

My absolute favorites are from this farm (their jelly donuts are also amazing)

HOT CHOCOLATE

Grab a hot chocolate (or hot toddy) at the Red Lion Inn and enjoy it on their front porch or in the cozy lobby

Shaker Village 

This was always one of my favorite places to visit when I was a kid; they have tons of different activities, classes and exhibits, but it's also just fun to explore

Museums  

A few to check out include MASS MoCA (plan to grab some bbq and/or a beer next door right after your visit, or grab a coffee from this coffee shop, who roasts their beans only a few miles away, that is located right at the museum), Clark Art Institute, Berkshire Museum, Crane Museum of Papermaking, Norman Rockwell Museum.

THE Mansions 

Many of the beautiful old mansions in the area have been transformed into spas, golf courses or hotels, but they're still pretty to drive by, and there are still plenty available for touring from Edith Wharton's home to Chesterwood to Ventfort Hall to Naumkeag. Be sure to check their calendars as many of them offer fun seasonal activities + events.