4 Best Restaurants in Sturbridge and The Pioneer Valley, Massachusetts

Donut Dip

$

This family-run business has been making doughnuts since 1957. Doughnut purists go there for the Old Fashioned Sour Cream, Apple Cider, and Honey Dip, but if you're feeling more adventurous there's plenty to choose from in the jelly, frosting, and sprinkles department, including a decadent bacon-topped creation.

1305 Riverdale St., Massachusetts, 01089, USA
413-733–9604
Known For
  • Old Fashioned Sour Cream doughnuts
  • friendly service—if you don't see a doughnut you want, ask for it
  • freshly brewed coffee

Flayvors of Cook Farm

$
The main advantage of stopping for the delicious homemade ice cream at this family farm is that you can see the dairy cows from the dining tables—and even pet them, if you're brave. Sandwiches and mac and cheese are available as well, if for some reason, you're not in the mood for ice cream.

Red Rose

$$

Featuring massive chandeliers, an open kitchen, and a large dining area, this half-century-old family restaurant is a big, brassy eatery where everyone from canoodling couples to huge parties can feel right at home. The menu features the usual gamut of Italian favorites such as the exquisite eggplant dishes, as well as a variety of pizzas made from a half-century-old recipe.

1060 Main St., Massachusetts, 01108, USA
413-739–8510
Known For
  • eggplant Parmigiana
  • primavera pizza
  • heaping platters of pasta
Restaurants Details
Rate Includes: Closed Mon., Tues., Reservations essential

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Whoopie-Doo & Cupcakes too

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This small bakery is big on cupcake creativity. Beyond your basic vanilla or chocolate, this spot offers flavors like Root Beer Float, Strawberry Crunch, and the occasional Unicorn Poop, which is a fun, colorful sprinkle concoction.