Sandy & Kevin
Things To Do
*Hilltop Orchards Winery & Cidery
Although lesser known, this spot is one of our favorites in all of Berkshires! Worth it every time for the wine & cider "tasting" (Sara will generously pour everything on the menu so you can try it all) and scrumptious apple cider donuts (don't be surprised if they pop in 2x the number of donuts ordered). Make sure to explore the expansive, dog-friendly orchards with a (very full) glass of wine or cider in hand!
*Tyringham Cobble Park
An easy-moderate, dog-friendly, 2-mile section of the Appalachian trail. Free admission and parking.
*Big Elm Brewing - Great Barrington Taproom
With two locations in Great Barrington and Sheffield, this brewery is an ole reliable with a great selection of brews. Dog-friendly, too!
Great Barrington Downtown
Great Barrington's downtown is an easy way to stroll through an afternoon. There are lots of shops, restaurants, and cafes with good eats and vibes!
Monument Mountain Reservation
Easy-moderate, dog-friendly trails under 3 miles. Parking fee. We have hiked these trails several times and love the incredible views throughout!
Balderdash Cellars
A well-known winery that is dog-friendly and BYOF!
Ice Glen Trail
A moderate 1.5 mile trail with fun rock scrambling and, at times, icy boulders. Dog-friendly, but this can be a wet and slippery hike.
Norman Rockwell Museum
A fun and interactive museum with beautiful grounds. Perfect for a slower morning or rainy day.
Barrington Brewery & Restaurant
An awesome solar-powered brewery with good grub! This is a really popular spot, so there may be a wait. Dogs are welcome in their outdoor seating area.
The Red Lion Inn
A historic spot to have dinner and drinks. We recommend checking out the live music downstairs at The Lion's Den!