A Massachusetts road trip and its prestigious Berkshires offers a perfect blend of breweries, museums, farm-to-table dining, and unique attractions. Here is my Western Massachusetts road trip itinerary that will guide you through must-visit spots in Springfield, Williamstown, Northampton, and the Northern Berkshires.
Start in Springfield – The City of Firsts
Springfield is a city of innovation and home to several iconic attractions is a great way to kick off your Western Massachusetts road trip. Begin your journey with some excitement at MGM Springfield, where you can try your luck at the casino or enjoy its entertainment offerings.
Springfield Museums
The Springfield Museums is a collection of five world-class museums of art, science, history, and Dr. Seuss. The museums include:
- Amazing World of Dr. Seuss Museum (and Dr. Seuss National Memorial Sculpture Garden)
- George Walter Vincent Smith Art Museum
- Springfield Science Museum
- Michele and Donald D’Amour Museum of Fine Arts
- Lyman and Merrie Wood Museum of Springfield History
We spent quite a good deal of time on the Dr. Seuss offerings but did briskly run through the art collections, which definitely deserve a peek. One ticket gets you into all five museums. The price is $25 for adults, $13 for youth, and $16.50 for college students and those over 60.
Naismith Basketball Hall of Fame
The Naismith Basketball HOF is a must-see attraction, even for non-basketball fans. It features 450 inductees, hands-on exhibits, and a 40,000-square-foot space filled with history. Test your skills at the Jerry Colangelo “Court of Dreams,”learn fun player facts, and immerse yourself in sports commentary.
Thanks for all the Jerry West references and memorabilia- this basketball legend went to my WV high school.
Pro Tip: Add on a few extra days to discover nearby Abington, Provincetown or Salem. Here are some suggestions for exploring Massachusetts Dog Friendly Day Trips.
Other Things to See & Do
- Six Flags New England – A thrilling amusement park experience.
- Mass Mutual Center – A venue hosting concerts, sporting events, and expos.
Where to Eat:
Breakfast is excellent at La Fiorentina. This family-owned Italian bakery offers incredible pastries, gourmet coffee and espresso, and savory options like omelets with homemade spicy sausage. You’ll most likely want to bring home some cookies and cured meats; the temptation is real.
For lunch, meet at White Lion Brewing, conveniently located downtown and offering chef-inspired elevated bar eats. Enjoy a wide selection of craft beer and delicious appetizers. I recommend the Pork Belly Burnt Ends and Fried Green Plantains.
An alternative lunch option is Nadim’s Downtown Mediterranean Grill, where you can savor authentic Mediterranean flavors at this locals’ favorite.
Twenty-two miles north, you’ll find 30 Boltwood, an upscale eatery inside a lovely luxury hotel (Inn on Boltwood) in Downtown Amherst. The Local Cheese Board is exceptional and delicious; you won’t want to miss this Instagram-worthy shareable.
Turkish Eggs and macaroni au gratin are tasty lunch options. The creative cocktails and zero-proofs pair wonderfully and elevate your dining experience.
Where to Stay:
- MGM Springfield – A luxurious casino resort with top-notch amenities. The progressive slots were really good; I’m saying this as a Vegas local.
- Marriott Springfield – Just an 8-minute walk from MGM, The Marriott offers comfort and convenience. You’ll find all the amenities you know and love in this enormous property with updated rooms.
Between Towns: Brake for Macarons in Bernardston
On your way to Northampton along your Western Massachusetts road trip, take a detour to Bernardston for a hands-on experience at Sweet Lucy’s Bakeshop, where you can partake in a macaron baking class. It’s great fun, and you’ll enjoy the camaraderie, learn some kitchen/baking skills, and take away some really great treats.
For dinner, dine at The Farm Table, a quintessential New England farm-to-table restaurant offering expertly crafted cocktails, flatbreads, and entrees. It is as beautiful to look at as it is to devour the tasty dishes.
My favorite eats were the Spinach Artichoke Dip, Fig Pig Pizza, and Farm Table Smash. Burger. If you’re there on weekends, enjoy the Sunday Brunch.
Next Stop: Northampton
Northampton is a charming town brimming with creativity, history, and fantastic food, and another excellent city to mark on your Western Massachusetts road trip.
Things to See & Do:
- Eric Carle Museum – A real hit for fans of children’s literature and illustration (picture book art). Having designed many classic children’s book artwork, you’ll recognize his methods at once. The museum has touring exhibits, an outstanding gift shop, and hands-on art offerings.
Where to Eat:
- HighBrow Wood Fired Kitchen & Bar – A local favorite known for its duck pizza (the best thing I ate on this whole trip!), famous sticky ribs, and rigatoni bolognese. Make a reservation—this is one popular hotspot.
Where to Stay:
- Hotel Northampton – A lovely historic property with elegant rooms, centrally located for exploring the town on foot. This property, a Historic Hotels of America member, focuses on attention to detail and has 106 guest rooms.
A Must-Visit Detour: Yankee Candle Village
One of the most shockingly amazing places you’ll ever encounter, Yankee Candle Village in South Deerfield is a massive shopping experience that caters to every possible need. From carefully curated gifts to an incredible selection of candles and interactive candle-making experiences, this stop requires several hours to explore fully.
It’s truly a one-of-a-kind destination that will leave you in awe.
Final Destination: Williamstown & The Northern Berkshires
Williamstown and its surrounding areas are home to some of the country’s best art museums and scenic landscapes. This is how I always pictured New England.
Things to See & Do:
The Clark (Sterling and Francine Clark Art Institute) is one of the most incredible art museums in the country, featuring a world-class collection and an on-site dining option. Expect to view magnificent paintings by Renoir, Degas, Homer, and even Remington, whom I didn’t realize did anything besides sculptures.
If you can get on a guided tour, I highly recommend it. Don’t miss the lovely china tea and saucer collections. Fun Fact: Admission is free in January, February, and March.
MASS MoCA – A contemporary art haven housed in a massive former factory space. This upcycled property is home to dozens of businesses, including Bright Ideas Brewing, serving some of the best stouts (Aztec Winter milk stout) and sours I’ve ever tried. The Czech’s Out Pilsner may change your mind even if you aren’t a beer drinker.
The brewery is pet—and kid-friendly and allows food to be brought in. It also serves root beer on tap and many non-alcoholic brews.
Where to Eat:
- Trail House Kitchen & Bar – A cozy eatery along the Mohawk and Appalachian Trails, offering delicious burgers, entrees (chicken cordon Bleu for the win!), and must-try pies.
- The Barn – A top choice for breakfast with a welcoming atmosphere. You can’t go wrong with the French Toast, but the Avocado Toast was the real winner for me.
Where to Stay:
The Williams Inn is a cozy yet stately inn in the Northern Berkshires featuring elegant common spaces, high-end dining, and thoughtful amenities like coffee and tea stations on each floor. The well-appointed rooms offer warm wood floors, luxurious linens, and modern conveniences.
This is a seriously gorgeous property (with a signature restaurant) that, if your budget can afford, you shouldn’t miss. And it had the best bed (Eurotop mattresses) I’ve slept in for ages.
Bonus Travel Tips
Traveling to Western Massachusetts or the Berkshires by bus? Peter Pan Bus Lines has been a trusted service provider in the Northeast for over 100 years, offering convenient and comfortable transportation options from New York, Boston, Philadelphia, and Washington, D.C.
Flying in? Consider arriving at Bradley International Airport (CT) and stopping at the New England Air Museum, which features incredible exhibits and dozens of military aircraft for aviation enthusiasts to explore.
Final Thoughts
A Western Massachusetts road trip (and The Berkshires) is a perfect getaway for those seeking culture, history, and incredible food and drink. From the vibrant city of Springfield to the artistic hub of Northampton and the scenic beauty of Williamstown, each stop offers something unique and memorable.
Thanks to Explore Western Mass for hosting my road trip adventures and introducing me to this unique slice of Americana.
Pack your bags and get ready to explore the best of Western Mass!
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