Western Massachusetts

When you visit Hampshire County of Western Massachusetts, the bustling downtown destinations only make up half the equation. There’s so much to discover beyond our city lines, particularly in the Hilltowns of western Hampshire County—Chesterfield, Cummington, Goshen, Huntington, Middlefield, Planfield, Westhampton, Williamsburg and Worthington.

This part of Hampshire County is home to Snow Farm: The New England Craft Program and countless other artists finding inspiration in the woods. Events like the Sevenars Concerts in Worthington or Huntington’s North Hall Arts Festival let you step back in time in old New England buildings while enjoying some of the finest arts and culture. There’s plenty of unique outdoor places to explore from the Chesterfield Gorge to the Keystone Arches in Middlefield. Plus the drive alone along the scenic byways in this region will surprise and delight you. 

Here’s just one possible weekend itinerary for a late summer visit to the Hilltowns in Western Massachusetts. Additionally, be on the lookout for some of our lesser known signature fairs and festivals like the Middlefield Fair August 12-14, 2016, Cummington Fair August 25-28, 2016, and the first annual Hilltown Chautauqua Earthcare Festival September 9-11, 2016. 

SATURDAY

Morning—Fresh Picked

Blueberry picking at Roberts Family Farm in Chesterfield

What better way to start the day than picking fresh fruits and vegetables? Right now is blueberry season and Roberts Family Farm is open Wednesdays through Sundays 9 a.m. to 5 p.m. If you have extra time, there’s even a miniature golf course on site.

Alternatively, you could spend the morning exploring what’s in season at local farm stands like the ones at Valley View Farm in Haydenville or Grace Hill Dairy Farm in Cummington.

Afternoon—Get Your Culture On

Visit the William Cullen Bryant Homestead and Kingman Tavern in Cummington

The William Cullen Bryant Homestead is one of over 100 Trustees of Reservations properties and a National Historic Landmark. The grounds of the Homestead are open year-round, but house tours and programming occur July-September. Depending on the day, you can enjoy a general house tour or an on-site historic play. Full details and schedule are available on the Trustees website. The Homestead is a great place to picnic, too! Be sure to stop at the Old Creamery Co-Op for sandwiches like The Spicy Maddow (yes named after Rachel Maddow) or the Hamalot.

Most small towns have a small one room historic museum, but Cummington's Kingman Tavern is an early 1800's house of 17 rooms, which served as a public tavern once. There is also a replica of a 1900 country store, a two-story barn, a carriage shed, and an 1840’s cider mill. Only open Saturdays in July and August from 2 to 5 p.m.

Visit Three Sisters Sanctuary in Goshen

Three Sisters Sanctuary is a place you have to see to believe. And with a two-story tall tinman out front, you won’t be able to miss it! The Sanctuary is roughly four acres of land surrounding the Good Time Stove Company featuring a constantly evolving and intriguing collection of gardens, environmental art, and installations. Open seven days a week, 8 am to 5 p.m.

Three Sisters Sanctuary, Goshen | Photo by Lynne Graves

Evening—Finish Fresh

Dinner at Bread Euphoria in Haydenville

Bread Euphoria is a great bakery escape during the day but sitting down for dinner there is a real treat, too, especially on a Saturday night when they have live music from 6 to 8 p.m. Enjoy some best artisnal pizza available in the region featuring the freshest local ingredients. 

SUNDAY

Morning—Fresh Baked

Breakfast and shopping at the Williamsburg General Store

Any time you pass through the center of Williamsburg, your trip should include a stop at the Williamsburg General Store. The General Store offers up a classic New England experience browsing unique wares and provisions. Be sure to start your day with the store’s signature baked goods, especially a “Wrapple."  While you’re at it, pop across the street to the Williamsburg Market and pick up lunch to enjoy at the state park later.

Afternoon—Explore the Great Outdoors

Visit the DAR State Forest in Goshen

At the DAR, you can enjoy a full day in the great outdoors. A day pass grants you access to swimming or paddle boating (w/ your own boats) on Highland Lake, aka "The Goshen Ocean," as well as miles of trails and plenty of picnic perfect spots.  Be sure to visit and climb the fire tower and take in 360 degree views of the surrounding hills.

Evening—Roadside Perfection

Dinner at Local Burgy in Williamsburg

Local Burgy is Northampton’s Local Burger’s food truck permanently located off Route 9 in Williamsburg. When you have to choose between smoked brisket and a lobster roll, you know you’ve arrived at a great roadside dining destination.

Ice Cream at Village Green in Williamsburg

Luckily dessert is only a few steps away! The Village Green has an assortment of homemade ice cream and soft serve in traditional flavors as well coffee and black raspberry. 

Looking for lodging ideas? Check out some of our quaint and peaceful Bed and Breakfasts.