Road Tripping Through the Pioneer Valley, in Search of America

Massachusetts' greatest gem.

June 18, 2019

Pack your bags! In honor of life’s most delicious highways, we give you Hit the Road, Snack, our travel guide of things to eat, see, and do this summer from coast to coast.

A look down on Holyoke, across the Connecticut River, South Hadley on the beginning rise, with the hills on the Eastern side of the Pioneer Valley behind it. Photo by Paul Cooper

Nestled around the Connecticut River valley in Western Massachusetts is an area known as the Pioneer Valley. Home to the Five College Consortium (that’s Smith College, Mount Holyoke College, Hampshire College, Amherst College, and the University of Massachusetts Amherst), the area’s local music, performance, and visual art scenes are quite rich. Plus, a good cup of coffee or independant bookstore are never far away.

Surrounded by the Holyoke and Mount Tom Ranges, the Pioneer Valley is ideal for hiking and biking; between the mountains you’ll find farms (many of which offer public apple, pumpkin, and berry-picking) and several quaint towns and small cities.

Each small town in the Valley is walkable, but you’ll have to get there first—and while many are less than a 15 minute drive from each other, most are connected by highways and long country roads. Amtrak trains and Peter Pan busses will bring you to the larger towns, and the area’s public bus system is convenient enough for car-less college students and those with short work commutes. But the best way to get around the Pioneer Valley when visiting is to drive yourself.


Known fondly as the best small arts town and one of the most lesbian-friendly cities in the country, Northampton is home to much more than Smith College. Pretty centralized in the Pioneer Valley, the town is packed with trinkets-filled shops, boutiques selling both hiking boots and sundresses, and dozens of quaint cafes, bars, and restaurants.

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“Anyone who drank in the Amherst bars in college knows that at last call you can always cut the line for HOT CHEESE UP FRONT.”
— Amanda

Grab a coffee and one of the best peach scones you’ve ever tasted at Haymarket Cafe to get your morning going. (You may want to stop back later, they’re open for lunch and dinner too.) Swing by the Smith College Museum of Art for an impressive collection of American, European, Asian, African, and Islamic art, as well as Greek and Roman antiquities and a by-appointment print center. A stop at Smith’s Botanic Gardens is also a delight if you’re into plants.

Scarf down a sandwich and a giant cookie at Woodstar Cafe, or dig into silky-smooth hummus, veg-packed tagines, and pillowy steamed eggs at Amanouz or Mosaic (they have essentially the same menus!). When it’s time for a cocktail, head over to The Green Room for a carefully constructed cocktails and an expansive aperitif bottle collection. For something a little more casual, explore The Dirty Truth’s host of rotating beers on tap. Want to play pool in a dive bar with $1 jello shots but also sip on drinks made with freshly squeezed orange and grapefruit juice? It’s Ye Ol’ Watering Hole or bust. Pick up a local-grain loaf (or, if you timed it right, a takeout pizza) for a car snack at Hungry Ghost Bread on your way out. Trust me.

A five-minute drive will take bring you to Florence, a tiny village in the northwestern part of Northampton. Grab a counter seat and a turkey club at the Miss Florence Diner, an eatery that’s been going strong since 1941. But save room for a slice or two at Florence Pie Bar, which rotates a menu of seasonal sweet and savory pies every two weeks! Then grab a pint or take a growler to go at Brew Practitioners, a mostly women-run business of beer lovers.

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Hop back in the car and drive 15 minutes to Easthampton. The formerly bustling mill town had a few slow years, but is quickly becoming home to a resurgence of young creatives who couldn’t bear to leave the Pioneer Valley after college—what used to be dilapidated giant textile and rubber factories have become artist studios, cultural hubs, and eateries. Start your morning with a warm croissant and coffee at Small Oven, and don’t skip a loaf multiple rotating daily bread offerings (hello, sesame wheat, three-seed sourdough, and local spelt rugbrod!). Explore some local shops, then pop into Daily Operation for a sandwich. Trade the car for a bike for an hour or two and explore the 6-mile Manhan Rail Trail. For dinner in Easthampton, the number one choice is always seasonal and charming Coco & The Cellar Bar.

Make a loop through some other small towns in the area, starting with Holyoke, 15 minutes from Easthampton. Hop out of the car the hike some of Mount Tom, 22 miles of trails and stunning views of the Valley. 10 minutes north is South Hadley, home to Mount Holyoke College. Pick up a few novels you’ve been meaning to read Odyssey Bookshop, then read a few chapters and fuel up at Thirsty Mind. Hadley is just up the highway—grab a snack at Esselon Cafe and, if it’s Sunday, spend an hour or two the Olde Hadley Flea Market.


Another 10-minute ride northeast will bring you to Amherst. Home to both Amherst College and UMass Amherst, it’s definitely a college town. But that doesn’t mean it’s all frat bros—Emily Dickinson’s former home is now a museum, and Hampshire College is just down the road, making Amherst businesses a unique blend of preppy and quirky.

Pop into the Eric Carle Museum (it’s on Hampshire’s campus) for hundreds of original Carle prints and numerous picture book illustrations from around the world, or peruse the Atkins Farm Country Market before driving into Amherst proper. Caffeinate yourself at Amherst Coffee, then explore the town—there are plenty of small bookstores, galleries, and shops, as well as an indie movie theatre—definitely don’t miss The Black Sheep for a sandwich. Come dinnertime, hit Mission Cantina for a casual burrito and margaritas.


25 minutes north of Amherst is Montague, a charming town home to the Montague Book Mill, offering thousands of used books, plenty of snacks, and one waterfall. Breakfast, lunch, and a rotating list of wine and beer are available at The Lady Killigrew Cafe, and if you stick around for dinner, The Alvah Stone’s creative New American food and cocktails are some of the best in the area.

Pop over to Deerfield (15 minutes from Montague) and spend a few hours in the 18th Century at the Old Deerfield Historic District. Drive a few more miles north to go antiquing in Greenfield, then hike up to Poet's Seat Tower for stunning views. Walk over the Bridge of Flowers in the village of Shelburne Falls (17 minutes west), then pop over to Baker Pharmacy for an old-timey soda fountain vibe.

Where to Stay

As mentioned, the Pioneer Valley is packed with college towns, so there are numerous moderately priced chain hotels throughout the area. If you’re looking for something a little more charming, check out the Hotel Northampton, the Inn on Boltwood, the Black Walnut Inn, Daniel Stebbins House Bed & Breakfast, and the Leyden Log Cabin.

Did we miss anything? Let us know in the comments below.

Hit the Road, Snack

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Rebecca Firkser is the assigning editor at Food52. She used to wear many hats in the food media world: food writer, editor, assistant food stylist, recipe tester (sometimes in the F52 test kitchen!), recipe developer. These days, you can keep your eye out for her monthly budget recipe column, Nickel & Dine. Rebecca tests all recipes with Diamond Crystal kosher salt. Follow her on Instagram @rebeccafirkser.


Hannah May 24, 2021
This is my homeland. I’ve been to a lot of excellent farmers markets and restaurants around here, including Coco and the Cellar bar. Their whole bar menu is par on and you will not leave there unhappy with your drinks. They offer a excellent food menu as well, and have come out with a cookbook that I’m very happy with-Curry & Kimchi-and the kids seem to be happy with it, too.

An even older market I hope never goes out of business is Fosters Market of Greenfield-you find a lot of products you might remember as a kid (I still get my Plochman’s Mustard there) and it’s so nice to get a Clark bar in a supermarket setting. I hope it never goes out of business, it’s a gem of a place for me.

Jessica - I don’t know if you know, but Wilson’s closed in Greenfield this year. It breaks my heart because I went there a lot through my childhood.

Amanda June 19, 2019
Oh, my heart breaks that there is no mention of Antonio's Pizza in Amherst! Hole-in-the-wall place serving some of the best pizza by the slice I've ever had (full disclosure: I'm a proud UMass alum but I've been gone for 17 years and I still go straight to Antonio's and buy enough to carry home with me anytime I happen to be in western Mass). They have an amazing array of interesting toppings, some of which changed the way my young self saw pizza, but always have the plain slices ready to go. Anyone who drank in the Amherst bars in college knows that at last call you can always cut the line for HOT CHEESE UP FRONT.
Jessica June 18, 2019
The best place to stay in Greenfield is the Brandt House and best place to eat dinner is Hope & Olive. Also check out Green Fields Market for lunch and the People's pint for great fresh beer. Wilson's department store is also worth a look.
Abgrundtieferbauch June 18, 2019
Perhaps it would make sense to accompany this article with a picture from the region, rather than some other place ostensibly out west? I also want to mention that there's an extensive network of bike paths, and it's nicer to bike between Northampton and Amherst than drive!
Abgrundtieferbauch June 19, 2019
Thanks for changing it!