Rte 20 Jacobs Ladder Scenic Byway

The Ultimate Fall Outing is Just a Short Drive Away

Up in the Hilltowns of Western Mass, we specialize in fall. From orchards to pumpkin patches, leaf peeping drives on three designated Scenic Byways (Rtes 20, 112, and 143) to hiking and kayaking, we have the best ingredients for a perfect fall getaway. 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.

Where are the Hilltowns?

The Hilltowns are the area between the Pioneer Valley – also called the Connecticut River Valley – 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. Check out our map and Guide to Fall Daytrips (we’d be happy to send you a copy) to see where each of our 29 villages are located).

Keystone Arch Bridges – Credit Chester Railway Station

What’s there to do?

Plenty in every season, but fall shows off our leafy best. There’s a reason New England is world famous for this!  Slow down on one of those three scenic byways – you will likely see vintage cars and motorcycles out for a spin – where each bend in the road reveals another stunning rock formation, scarlet and gold leaves and tumbling streams that all feed into the Wild & Scenic Westfield River.

History and railroad buffs marvel at the Keystone Arch Bridges, an engineering feat of the world’s first mountain railway built without mortal that still keep trains on track. You can learn about local railroad history at the Chester Railway Station & Museum..

Littleville Lake – Huntington

For information on 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.

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 an on-site cabin and even bring your dog.

Kayakers love the lake at the DAR State Forest. Littleville Lake and the Otis Reservoir are great for a leaf-reflecting paddle. Ponds are everywhere! The Hilltowns offer some of the best trout fishing nationally in spring along the Westfield River, but in fall people who fish are still catching stripers and sunnies. An interactive fishing location map from the state government is here.

Apple Picking – Credit Libby Meehan

Kids go nuts for fall in the Hilltowns

You’ll skip the long drive and thrill your kids if you choose the Hilltowns for your fall weekend getaway. Jameson’s High Meadow Farm, Outlook Farm Barn & Eatery, Mountain Orchard and West Parish Orchard offer plenty of chances for tasting, picking and snapping the ultimate fall photos.

Kid-friendly walks include the Littleville and Knightville Dam recreation areas, Rivulet Trail, Sanderson Brook Falls, the Becket Quarry and The Chesterfield Gorge, The Keystone Arch Bridges trail. They’ll enjoy the many boulders to climb on and rocks to skip.

For an unforgettable experience, go on a Hilltown Sleddogs ride as the leaves fly. 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 and Halloween related activities like haunted walks is the Hilltown Families newsletter. It’s free.


Comfort Kitchen and Bar – Huntington

We need to eat…suggestions?

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

Breakfast is amazing on the deck overlooking Chester at Carm’s, which is an updated take on a classic diner. We love the Chesterfield General Store, The Outlook Farm Barn & Eatery, The Old Creamery Co-Op, The Williamsburg General Store and the Breadbasket Bakery in Russell for coffee, pastries and breakfast and lunch sandwiches. Look out for cider donuts and apple pies to go.

Fall is the perfect time for a picnic. Pick up provisions at all of the above and head to one our state parks with a blanket. Many of the turnoffs along the scenic byways have picnic tables. (Just make sure to carry out your trash. One of the reasons our region is so beautiful is that we all take care to clean up after ourselves.)

For dinner, The Comfort Kitchen & Bar in Huntington and the Chester Common Table offer casual dining in historic settings.

Sena Farm Brewery – Credit Daily Hampshire Gazette

I want a drink after a long day of looking at all those leaves, is that possible?

Absolutely! Glendale Ridge Vineyard in Southampton looks like you’re in Napa, but with views of Mt. Tom. They are introducing their latest vintage of Sauvignon Blanc and Rose and often have food trucks and live music.

Sena Farm Brewery in Worthington will serve you up a wild fermented ale using fruit from local farms and wildly harvested yeast, creatively crafted IPA’s, Lagers, Stouts, and Belgian style ales.

The Blandford Fair

Meet a farmer, taste their wares.

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 and produce from their gardens. Oliver’s Farm Stand and Earth Song Farm and Farm Stand are great examples of this. 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. Some have sugar shacks for country breakfasts in spring, but then we are getting ahead of ourselves.

DeVries Fine Art Sculpture Trail – Andrew DeVries

We likely have as many artists as we do farmers.

There is something about rural beauty, plus a huge old barn, that inspires nationally-known artists to move to the Hilltowns. The weekend of October 1st and 2nd is the Hilltown Open Studio Tour where you can meet 24 artists and check out their work and way of life. Take a walk in nature and see sculpture at the Andrew DeVries River Studios Sculpture Trail, Three Sisters Sanctuary or in the Cummington Cultural District. Artist Kathryn Jensen produces a calendar each year of scenes from the Hilltowns.

The Bread Basket – Russell


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 Bread Basket. The Swinging Bridge Auctions is worth a hunt for the next edition of Antiques Roadshow.

Gateway Farm & Pet has the perfect gift for your dog, cat or lama, plus rural themed toys for kids, garden shoes with chickens on them, mums, pumpkins, Halloween yard art and an entire room of Carhartt. Buy a quality hoodie or wool socks to stave off that fall chill!

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

The Goldenrod Country Inn – Worthington

Stay for the weekend

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 has just reopened under new management. 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.

You’re sold…how do you find a house?

The Hilltowns are an amazing place to live whether you are looking for your first home, a 2nd home getaway or a rural place to retire. We have excellent modern but uncrowded schools like Gateway Regional and Hampshire Regional. Property taxes are relatively modest. With broadband now covering the Hilltowns, people are working remotely or able to do hybrid work with more space than in either the Pioneer Valley or the Berkshires. It is still possible to buy waterfront property on our many rivers, lakes and ponds.

Realtors like Kim Bergland, Carol Saltus, James Molyneux and Linda Webster all have the right contacts and properties to help you find the perfect place.

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: visit@hilltowndirectory.com. If you are interested in advertising, go to hilltowndirectory.com/adopportunities