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Weekend Getaway: The Pioneer Valley, Massachusetts

Weekend Getaway: The Pioneer Valley, Massachusetts

The bucolic area tucked between the Berkshires and Central Massachusetts is filled with colleges, farms, and great places to eat.

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Amy Cavanaugh
Jul 04, 2025
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Weekend Getaway: The Pioneer Valley, Massachusetts
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Hot dogs from Nick’s Nest. (Photo: Kenney Marlatt)

Welcome to the holiday weekend!

In today’s newsletter, we’re off to a very special place — Amy’s hometown! The Pioneer Valley in Western Massachusetts includes the cities and towns of Holyoke (where Amy is from), Springfield, Northampton, Easthampton, Amherst, and many others. This is an area with a great food scene (that’s in large part due to all the farms providing local produce, and the colleges bringing an international perspective), so we’re going to check in on some favorites, including a hot dog stand we never miss, a classic doughnut shop, and one of our favorite cocktail bars anywhere.

After you’ve read the story, download our Field Guide to the Pioneer Valley, which organizes all our picks into a three-day itinerary. We’ll tell you where to go for coffee, breakfast, lunch, drinks, and dinner. Plus, each guide includes links to Google maps and Instagram and is downloadable for offline reading. The Field Guide to the Pioneer Valley is free to paid subscribers, but can also be purchased on our website for $10.

Before we sign off for the weekend, we’ve put together a Weekend Reading list with affordable cocktails, affordable getaways, and news of a somewhat-less affordable chef’s tasting menu coming soon to Philadelphia.

Thanks for reading!

— Amy Cavanaugh & Kenney Marlatt


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Downtown Northampton, Massachusetts. (Photo: Kenney Marlatt)

Hometown Favorites

PIONEER VALLEY, MASS. — When I talk to people who grew up in other parts of the country, I’m often surprised at how little international food they had access to. In the Pioneer Valley where I grew up, we had Mexican and Chinese, Thai and Japanese, Moroccan and Greek, Cajun and Indian, Puerto Rican and Argentinian, and on and on. That’s nothing in a big city, of course, and times are changing now, but this part of Massachusetts has been enjoying cuisine like this for decades.

When people ask me where I’m from, I say Western Massachusetts, along the Connecticut River Valley, between the Berkshires to the West and Worcester to the East. If you’ve only been to Boston, that’s an hour and a half East of here. There are rolling mountains, dairies, and farms (the area is famous for its asparagus, called Hadley Grass), and lots of colleges. I went to Mount Holyoke College, but took classes and spent time at the University of Massachusetts, Smith College, and Amherst College, which keeps the towns of Amherst and Northampton full of interesting things to do.

People visit this area to hike the Mount Tom Range, see the foliage in the fall, visit the Basketball Hall of Fame in Springfield and the Volleyball Hall of Fame in Holyoke (the sports were invented here), and explore the great towns. Northampton would make a fine home base (stay at the Hotel Northampton), though our itinerary will also take you to Holyoke, Easthampton, Springfield, and beyond.

The sun sets over Easthampton, Massachusetts. (Photo: Kenney Marlatt)

In our three-day itinerary, we’ll hit a maple sugaring breakfast, grab burgers for lunch, go for sushi, and do much more. There are more great places here than we could fit in our guide pages, but we’ve put together our can’t-miss spots, starting with our favorite coffee shop.

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