The winding road through the pines on Route 202 is the highlight of your drive into the Pioneer Valley. Stop off at the Quabbin Overlook in New Salem, Massachusetts to take in the full scope of the Quabbin Reservoir. A short, flat trail brings you to a scenic vista of the 39-square-mile man-made lake, where four towns were flooded to create the Greater Boston water supply. Nowadays, the Quabbin is a hub for recreation and wildlife—you may even glimpse a bald eagle soaring over the watershed.

The friendly college town of Amherst, Massachusetts is an inviting place to stop for a break.
Explore the town’s literary history with a walk past the Emily Dickinson Museum on Main Street. It includes two historic houses, the Homestead and the Evergreens, where the poet and her family lived during the 19th and early 20th centuries. The museum's mission is to bring Emily Dickinson's revolutionary poetic voice to life in the very place she called home. The museum offers tours of the famously reclusive poet’s home. Plus, they have a great bookshop, too!
You can also stroll the scenic grounds of Amherst College. Or, simply grab a coffee and a treat from the Black Sheep Deli and Bakery and watch the clouds float by in Amherst Common.

There are countless dining and drink establishments tucked into brick facades of Northampton’s main drag, but for fans of Mexican food, La Veracruzana is a local standby.
This colorful establishment serves up everything from casual tacos and burritos to enchilada plates that are fancy enough to celebrate a special occasion. Top off your lunch with a house margarita, and don’t forget to try the variety of unique salsas at the fresh salsa bar. One perk of the COVID-19 pandemic: La Veracruzana now offers outdoor seating.

Historic Deerfield is a well-preserved colonial village on the Deerfield River, where tensions between European settlers and the Native peoples of New England came to a bloody head in the infamous raid of 1704.
Now the historic village offers a fascinating glimpse into New England life in the 18th century. Visitors can view the collections at the Flynt Center of Early New England Life, tour the Old Burying Ground, or sample heirloom plants at ​​an open hearth cooking demonstration.

There are myriad reasons to visit the quaint riverside village of Shelburne Falls, Massachusetts, which is listed on the National Register of Historic Places, but most summertime visitors are garden enthusiasts who come to see the Bridge of Flowers.
This pedestrian walkway is adorned with a colorful array of seasonal plantings, from bright blooms to lacy tendrils overhanging the river. Admission is free, but donations help keep this volunteer-run operation blooming year after year.

Use this parking lot to visit a magnificent sculpture park full of enchanting artwork.

If you're a fan of Dr. Seuss, then you won't want to miss this National Memorial Sculpture Garden. It's a beautiful outdoor space filled with over 30 bronze statues of your favorite characters from his books, created by his stepdaughter, Lark Grey Dimond-Cates.

Before you leave the Pioneer Valley, stop off at the Red Rose Pizzeria. This spacious brick dining room — founded by an Italian family in 1963 — is known for its crisp yet chewy crust. Other options include pasta, seafood and chicken plates, and grinders. For a large party, get a sheet pizza to share family-style.