Wild & Scenic Westfield River

Up in the Hilltowns of Western Mass, winter can be dazzlingly white and offers a quiet escape. Farms have long since plowed their fields under, artists are heating their studios with woodstoves and the last of the leaves cling to our hiking trails. If you’re prepared for it, the Hilltowns offer a wonderful day out with a bundled-up walk followed by lunch or dinner at a restaurant in a historic building. 

Our lakes and ponds freeze over and are perfect for ice fishing and skating in nature – just be careful and watch the signs about ice depth. Snowmobiling, snowshoeing and cross country skiing opportunities abound.

Take a drive on one of our three designated Scenic Byways (Rtes 20, 112, and 116) and stay for a weekend. Best of all, we’re just 30 minutes away from Springfield, Northampton, Lee, Lenox and Pittsfield. With historic white-steepled villages, everything from short family walks to challenging hikes and a river so beautiful the National Park Services calls it Wild & Scenic, you can come for a day or stay for a life.

Littleville Lake

Where are the Hilltowns?

The Hilltowns are the area between the the Connecticut River – and the Berkshires. The Mass Turnpike borders us to the south and Rte 2/The Mohawk Trail to the North. There is no exit on the Turnpike for 35 miles between Westfield and Lee and that is part of what makes us so special: modern life largely passed our villages by. You will not find a single strip mall throughout our region. (Check out our map to see where each of our 29 villages are located). 

What’s there to do?

Take a Drive: Winter is wonderful for those intrepid souls who love to bundle up and partake in the beautiful hush of winter. Slow down on one of our scenic byways where each bend in the road reveals another stunning rock formation glistening with beards of icicles.

Chester Keystone Arch Bridges

Check out local history: History and railroad buffs marvel at the Keystone Arch Bridges, an engineering feat of the world’s first mountain railway built without mortar in the 1830s that still keeps trains on track. Many of our villages date to the 18th century. Graveyards attest to the lives of colonial era pioneers who built mills along the river and moved all those stones to farm a post glacial area.

Visit Rhoda Rhoades last resting place near the graves moved to Norwich Bridge Cemetery in Huntington when the building of the Knightville Dam forced out both the living and the dead from the village of Indian Hollow. She was a Native American healer with an interesting life story. To increase your understanding of the Indigenous peoples like the Mahicans and the Pocumtuc, who populated the area for thousands of years, this article is very helpful

Go Winter Hiking In the Hilltowns

Go for a hike: It’s never too cold to hike if you are bundled up. For information on winter hiking, check out the Hilltown Land Trust or The Trustees of Reservations which manages properties like the William Cullen Bryant Homestead Rivulet Trail, the Becket Quarry and the Chesterfield Gorge. Our favorite waterfalls are Glendale, Sanderson Brook and Windsor Jambs. They look like they explode with crystals when winter covers them in ice.

The Western Mass Hilltown Hikers are extremely active and lead group tours that highlight both natural beauty and local history. They also publish hiking maps. At the Appalachian Mountain Club’s Noble View you can stay the night in a toasty on-site cabin and even bring your dog.

Go Ice Fishing: Ice fishers love the lake at the DAR State Forest. Littleville Lake and the Otis Reservoir where stripers, sunnies and trout are down there somewhere. An interactive fishing location map from the state government is here.

Snowmobiling Abounds: The Hilltowns are filled with snowmobile possibilities. Check online or with The Hilltown Snowmobile Club for best options.

Cross Country Ski or Snowshoe: Those who like backcountry head for our state forests or frozen lakes like Littleville or Ashfield, or the Knightville Dam recreation area to make their way. If you are looking for groomed trails, there is no better place than Notchview, which is managed by the Trustees of the Reservations. There are 3000 acres and terrain for all skill levels. They also have rentals and lessons. Certain trails are dog friendly.


Cross Country Skiing in the Hilltowns

Maple Corner Farm in Granville enables you to cross country ski and snowshoe with 20 km of groomed trails on varied terrain and separate snowshoe trails.

Skate in Nature: There are frozen ponds everywhere and the ice at places like Littleville Lake get to 18 inches thick but always best to go with someone who knows. Join the Western Mass Ice Skaters group on Facebook for updates on the best of nature’s rinks.

Downhill Skiing is Close: Stay in the Hilltowns for the weekend and ski at Berkshire East Mountain Resort in Charlemont, the closest downhill mountain. It’s easier to get to and less crowded than the Vermont resorts.



Kids Enjoy Winter in the Hilltowns

Courtesy Hilltown Families

You’ll skip the long drive and thrill your kids if you choose the Hilltowns for a winter weekend getaway. Kid-friendly walks include the Littleville and Knightville Dam recreation areas, Rivulet Trail, Sanderson Brook Falls, the Becket Quarry and The Chesterfield Gorge or the Keystone Arch Bridges trail. Stop at Pat’s in Wiliiamburg and Gateway Farm & Pet for those all important Yaktrax: pull-on coiled magic for your boots that will keep you from slipping. 

Courtesy Hilltown Families

Many Hilltowns have designated sledding hills and create outdoor rinks by flooding conducive areas. Check the town websites or the Hilltown Families newsletter.

For an unforgettable experience, go on a Hilltown Sleddogs ride through the snowy woods. Finally ready to get that family dog? Hess Family Beautiful Puppies raises mini goldendoodles. Call ahead to pick yours.

The best way to find out about kid-friendly fun is the Hilltown Families newsletter. It’s free.

Fuel Up With Comfort Foods

You won’t find ANY chain restaurants here, but we have general stores with bakeries, and cozy restaurants with home-cooked local foods.

High Hopes Farm Sugar Shack Breakfast

Breakfast and Lunch is amazing in Chester at Carm’s, which is an updated take on a classic diner. We love the Hungry Man breakfast where you get two meats, pancakes, eggs, home fries – we won’t even tell you how reasonable the prices are..You’ll also find home baked goods, lattes or the now nearly forgotten bottomless cup of house coffee.The Chesterfield General Store makes a mean deli sandwich, whoopie pie, and oh the cheesecake. 

Stop at the The Outlook Farm Barn & Eatery on Rte 66 in Westhampton for their house smoked meats, ciders, wine, beer, plus breakfast and lunch at the deli until the end of January when they take a pause till AprilThe Old Creamery Co-Op in Cummington makes a mean panini, sells local goods from artisans and is open to all, not just co-op members. 

The Williamsburg General Store has everything you didn’t know you needed from days of old, and wrapples, a pastry stuffed fruit goodness that’s a local tradition. 

The Breadbasket Bakery in Russell is open by 5:30 AM for coffee, pastries, breakfast and lunch sandwiches. It also stocks goods for baking, their own jams, syrups and sauces made here by members of our local Mennonite community. Buy one of their frozen fruit pies made from the local orchards and pop it into your oven. They also sell unique birdhouses and hand-crafted wooden furniture.

Comfort Kitchen & Bar

Dinner: The Comfort Kitchen & Bar in Huntington offers casual dining in a historic settings. We especially love their use of local ingredients and the fact they offer comfort foods like chicken pot pies and meatloaf. The Chester Common Table is right across from the historic train station in Chester and was an old railroad inn. Now, you’ll find great local inspired dinners and locals will likely turn up and play folk music until they close.

Goldenrod Country Inn

Our two newest restaurants are both in Worthington. The Goldenrod Country Inn has brought much welcomed exuberance to the central Hilltowns and brought us our first ever drag brunch this past fall. They also were the hub for an epic Zombie Pub crawl this Halloween and had visits with Santa and a wreath and sip event this Christmas. Like them on Facebook to keep up with their latest menu additions and events. (We are partial to their whitefish chowder, vegan ravioli, pot roast and that swordfish with chutney.)

Liston’s Bar & Restaurant  is the recreation of a famous local roadhouse opened in an old gas station in 1933. The menu has been updated and you can enjoy a beer or a cocktail with a house burger or a steak and cheese grinder with hand-cut fries 

I want a drink after a long day of snowshoeing.  Is that possible?

Glendale Ridge Vineyards

Absolutely! Glendale Ridge Vineyard in Southampton looks like you’re in Napa, but with views of Mt. Tom. Their 2022 vintages are really amazing due to all that hot, dry weather we had this summer.. Explore wines made with local grapes developed by Cornell University just for our unique terroir (that’s fancy French for the local geography and geology) such as Corot Noir and Traminette.

Jared Sena of Sena Farm Brewery

Sena Farm Brewery in Worthington offers their latest creative beers including IPAs that are infused with ingredients like local hops and raspberries. The barn/taproom is an amazing hang out spot on a cold winter night.

Papa Bob’s on Rte 20 in Becket features local beers, weekend music and roadhouse style food including pizza and shepherd’s pie. They are open weekends until the nearly unheard of Hilltown hour of 1PM.

Meet a producer, taste their wares.

Take Real Maple Syrup Home

The Hilltowns are distinctively rural for a reason. Many towns are “right to farm” with people setting up small local farms to raise everything from beef, pork and lamb to organic vegetables and medicinal herbs. There are both large farmstands and small self-service huts where people sell local eggs, jam and pickles made from their gardens.We suggest you bring a cooler and stock up on local, sustainably raised meats (check out Bridgemont Farm and Outlook Farm Barn) and cheeses. We suggest you bring cash as self service stands often collect money via the ancient exchange format of an old coffee can.

What trip to rural New England is complete without maple syrup? Stock up at Dufresne’s Sugar House, Maple Corner Farm or Paul’s Sugar House. High Hopes Farm in Worthington has announced their early spring sugar shack breakfasts: an all-you-can-eat buffet with their own maple syrup weekends starting February 25th. Put on your mud boots and enjoy some pancakes.

We likely have as many artists as we do farmers.

Andrew DeVries Sculptor

There is something about rural beauty, plus a huge old barn, that inspires nationally-known artists to move to the Hilltowns. Take a walk in nature and see sculpture at the Andrew DeVries River Studios Sculpture Trail, Three Sisters Sanctuary or the newly designated Cummington Cultural District. Main Street Cummington features installations by local artists and much more as the special designation – and new arts programming – goes into effect this spring. The Becket Arts Center’s gallery space is primarily open summer through fall but has periodic performances, community dance classes and more. Their gift shop offers original artwork and crafts from local artists. Check their schedule online.

Miss Comet by Sergei Isupov – Cummington

Need to get out of the house and do something artistic yourself? Check out the programs at the Snow Farm which runs the New England Craft Program. They have spring and summer classes in ceramics, jewelry, woodworking and glassmaking among other disciplines in Williamsburg.

Artist Kathryn Jensen produces a calendar each year of scenes from the Hilltowns. 2023 is available now!. And make sure to mark your calendars for the first weekend of October when the Hilltown Open Studio Tour happens. You can meet more than two dozen artists and check out their work and way of life. 

Shopping? Escape the mall and buy local.

Chesterfield General Store

No malls or chain stores here. What we do have is homecrafted goods like jams, candles and local artisan jewelry sold at the Chesterfield General Store, The Old Creamery Co-Op, The Williamsburg General Store and The Breadbasket. The Swinging Bridge Auction House in Huntington is worth a hunt if you are interested in appearing on the next edition of Antiques Roadshow or need help clearing out antiques from grandma’s house.

Need the perfect Christmas tree with a chaser of local honey and candles? Rockhouse Ridge Farm in Huntington has a picturesque setting, perfect blue spruces, bees and balsams plus gifts.

Gateway Farm & Pet

Gateway Farm & Pet has gifts for your dog, cat or wild bird, plus rural themed toys for kids, warm winter boots and an entire room of Carhartt. Buy a quality hoodie or wool socks to stave off that winter chill! The all important Yaktrax for your boots come in every version or size. The coil ones are for winter hiking, the spikes for walking on frozen lakes.

Pat’s Package Store on Rte 9 in Wiliamsburg packs more than just liquor. There is a room of local artisan wares, workwear including jeans and Carhartt. Warm up with some new flannels – or bourbon.

The Montgomery Marketplace has the Montgomery Grill that makes breakfast and lunch as well as a shop with locally made handicrafts that also teaches pottery.

Speaking of chills, the Good Time Stove Company can sell you a vintage wood stove or repair any type of stove at all.

Goldenrod Country Inn

Stay for the weekend – or put up your pet

Want to just get away for an entire weekend but don’t want to spend it driving? The Hilltowns are perfect for that. Wake up to the birds and take a walk in nature right from where you are staying. The historic Goldenrod Country Inn reopened in 2022 under new management with charming spruced up rooms. Inn Nature is a private accommodation with hiking trails. Rent an entire house in Plainfield for the family with access to hiking trails. The Singing Bridge Performing Arts Lodge has rooms in an 1800s location with live music on weekends.

Courtesy Hilltown Families

Want to take a weekend escape elsewhere but don’t want to bring your dog? The Bed & Bowl Bed & Breakfast for Dogs on County Road in Huntington treats your pup like a member of the family.

Huntington community services are here to help!

We know that our long cold winters can be challenging for many. It Takes a Village offers free infant, child and mom goods plus classes for parents. It’s a super fun, friendly environment that has taken over a historic church in Huntington. Parents “shop” the free goods and there are areas where kids can play inside. The Hilltown Pantry in Goshen offers food to residents of 10 Hilltowns Wednesdays from 1 – 3PM.

We’d love to hear from you! 

Anything we missed in this article? Submit your favorite things to do in the Hilltowns with a description and photo to: vist@hilltowndirectory.com. If you are interested in advertising, go to hilltowndirectory.com/adopportunities