Peak Experiences in the Hilltowns

By Sienna Wildfield as told to Jenny Miller Sechler | Illustrations by Alli Howe



When western Massachusetts residents refer to “the Hilltowns,” they don’t always agree on the details. The term commonly refers to a cluster of rural communities bridging the Connecticut River Valley with the Berkshire Mountains, but the towns deserving the official “Hilltown” stamp differ depending on the source.

Towns that usually make the list include the communities of Ashfield, Chester, Chesterfield, Conway, Cummington, Goshen, Huntington, Middlefield, Williamsburg, Windsor, and Worthington, but there at least another dozen that could be included in the roster.

While the Hilltowns boundaries can be argued, everyone can agree that the Hilltowns are a wonderful place to visit. Opportunities for outdoor activities are abundant. The Hilltowns host many beloved family events, such as the Cummington Fair and the Maple Fest in Chester. And the Hilltowns are also home to a variety of family-friendly destinations, with menus to tempt the palates of children and adults alike.



As the founder and director of Hilltown Families and a former chef and baker, West Chesterfield resident Sienna Wildfield is the ideal person to turn to for Hilltown recommendations. When it comes to food, Sienna prefers organic, locally grown produce and maintains a gluten-free diet.

Sugar Season 

The Hilltowns are a great place to be during sugaring season. The sight of the area’s numerous sugar shacks issuing clouds of steam into the cold sky is a sure sign of the coming spring thaw, as well as a way to identify delicious breakfast options.

Red Bucket Sugar Shack

584 Kinnebrook Rd., Worthington ◆ 413-238-7710 ◆ Find them on Facebook here

The Red Bucket serves a variety of both traditional and creative versions of pancakes and French toast. Last season’s pancake flavors included cranberry orange and pumpkin, and the restaurant’s almond French toast is a signature dish. If the kids haven’t had enough sugar with their breakfast, they can take home a bag of maple sugar cotton candy. And customers shouldn’t be deterred by the wait for a table, as it gives everyone a chance to observe the sap boiling down.



 South Face Farm

755 Watson Spruce Corner Rd., Ashfield ◆

South Face is another Hilltown institution, serving waffles, pancakes, and French toast made with homemade bread topped with maple syrup boiled down that very morning, alongside other breakfast fare and the restaurant’s signature corn fritters. South Face prides itself on supporting other local farms by using local eggs, milk, and blueberries. The restaurant also features maple milk shakes made with Bart’s ice cream. In addition to the restaurant, the sugar house is always open for visitors during the sugaring season.

Annual Maple Fest More

Chester◆ More information here.

An annual event held in March, featuring local artisans and a pancake breakfast. This year’s event takes place on March 21. The festivities start at 9am and the fun continues until 3pm.



Year-Round Destinations

Elmer’s Store

396 Main St., Ashfield◆

Described on their website as a “big time breakfast and Friday night dinner joint, Old Timey Natural Foods Grocery, and Art Gallery,” Elmer’s boasts delicious pancakes (including gluten-free), hot drinks (notably chai) and kid-approved ice cream sodas. Elmer’s popular breakfast menu is consistent, while their equally popular dinner menu offers new items every week.

Country Pie

343 Main St., Ashfield413-628-4488Find them on Facebook here

According to Sienna, her family will face a blizzard to pick up a pizza from this Ashfield establishment. Customers can choose from a wide array of fresh toppings or try one of the restaurant’s famous specialty pizzas, as well as widely praised sandwiches and wraps. The only catch for Sienna? The Country Pie currently doesn’t offer gluten-free products.



Bread Euphoria

206 Main St., Haydenville413-268-7757

Known for their amazing pizza (including “the best gluten-free pizza,” according to Sienna), pastries, and artisan breads, Bread Euphoria is a family friendly place to have a great dinner, sometimes accompanied by live music, or al fresco when the weather cooperates. Bread Euphoria uses organic and locally grown ingredients whenever possible, and describes itself as “proud to belong to a community of small farms and locally grown food producers.”

Old Creamery Co-op

445 Berkshire Trail, Cummington413-634-5560◆

The Old Creamery is a community hub for the Hilltowns, and with its expansive deli selection and yummy soups, it offers something for everyone, even the pickiest among us. The Old Creamery prides itself on using locally grown ingredients, as well as supporting local artists—the store’s inventory includes ceramics and paintings by Hilltown artists. Sienna’s family loves their hot chocolate, making it a popular place to stop after outdoor winter activities.



Additional spots to visit

The DAR State Forest

78 Cape St., Route 112, Goshen ◆ More information here

The DAR State Forest, initially donated by the Daughters of the American Revolution, features 15 miles of hiking trails, a lake for swimming in the summer and ice skating in the winter, and a fire tower with views of the area. The DAR campground is also a popular camping destination for family weekends. For a perfect winter family activity, Sienna recommends a hearty breakfast at one of the sugar shacks, an ice skating trip at the DAR with a stop at the warming hut, finished by a trip to the Old Creamery for hot chocolate.

Chapel Brook

Williamsburg Road, Ashfield ◆ More information here

Chapel Brook is a popular place to cool off in the summer months. This little patch of woods run by the Trustees of the Reservations is particularly known for a series of waterfalls, cascades and pools that provide a natural water slide. For a longer day, you can hike or snowshoe from Chapel to the DAR along a series of trails created by the Ashfield Trail Committee and then head to the Country Pie or Bread Euphoria for a pizza!



Chesterfield Gorge

River Road, Chesterfield ◆ More information here

The Chesterfield Gorge is a dramatic 70-foot-high canyon carved over centuries by the Westfield River. After making its way through the Gorge, the river opens up into a beautiful spot for bathing and fly fishing. The Gorge is a popular place for (un-groomed) cross-country skiing and snowshoeing in the winter.




Route 9, Windsor ◆ More information here

Notchview provides more than 17 kilometers of groomed trails for cross-country skiing, as well as back-country trails for more intrepid skiers and snowshoeing. Skis can be rented on site. Sienna also recommends Notchview as a great place for stargazing.

Sienna Wildfield is the founder and executive director of Hilltown Families, an award-winning online grassroots communication network serving thousands of families living throughout western Massachusetts. Sienna is a board member of the Hilltown Community Development Corporation, executive producer of the Hilltown Family Variety Show (103.3 FM Northampton, MA), a life-long activist, a mother, and an active community member living in West Chesterfield. See Sienna’s TEDx Talk, “Supporting Education Through Community Engagement” here.

Jenny Miller Sechler is a writer focusing on local, sustainable agriculture and the arts. She lives in western Massachusetts. Find her at

Alli Howe is a flower farmer from New Hampshire. She studied art at St. Lawrence University in Canton, NY. Find her at or see more work @aehowe08 on Instagram.