How to Plan the Best Boston to Wallingford, CT, Roadtrip

With picturesque vineyards, peaceful parks, and delicious cuisine, Wallingford, Connecticut, is a dream travel destination. For those living in Boston, it’s just an easy two-hour drive away! If you’re in need of a break from the busyness of Boston, escape to Wallingford for a romantic, relaxing weekend. We’ve provided how to plan the perfect roadtrip from Boston to Wallingford, CT below! For more things to do during your stay, be sure to access our free Vacation Guide. We’ve included dozens of recommendations on activities and attractions in Wallingford.

How to Plan the Best Boston to Wallingford, CT, Roadtrip

Where to Stop Along the Way

If you’re looking for a good place to stretch your legs during your roadtrip, you’ll find a couple of great breweries about halfway to Wallingford. Treehouse Brewing Company in Charlton may be small, but that’s not to say it doesn’t have a great selection of beer. Another wonderful option, Altruist Brewing Company in Sturbridge offers handcrafted beer and a welcoming environment. Be sure to check the breweries’ hours before your trip to ensure they’re open.  

Things to Do in Wallingford

While in Wallingford, spend some time exploring one of our region’s local vineyards. Gouveia Vineyards features a hilltop tasting room with stunning views, a cozy atmosphere, and world-class wine. Plus, it’s just minutes from downtown Wallingford! Paradise Hills Vineyard is a slice of Tuscan heaven and family-owned vineyard located on 65 acres of rolling green hills. Enjoy a year-round tasting room, wonderful views, and plenty of delicious wine.

In addition to vineyards, our town features a number of wonderful parks and outdoor spaces. Visit Wadsworth Falls State Park for hiking, swimming, and beautiful waterfalls! Another one of our favorite parks is Quinnipiac River State Park, which is home to fascinating wildlife, miles of hiking trails, and scenic marshlands. If you’re interested in exploring the surrounding nature but want to leave the planning up to us, our Hiking Package is perfect for you! Enjoy a picnic for two, bike rentals, a hiking map, and more.

Places to Eat

No trip to Wallingford is complete without sampling some of the area’s delicious cuisine. From open-air cafes and taco joints to authentic Italian restaurants and fine dining establishments, there’s something to satisfy every kind of craving in Wallingford. Our Vacation Guide is full of delicious restaurants, but some of our favorites include:

  • Michael’s Trattoria
  • J Christian’s
  • Archie Moore’s Bar & Restaurant
  • Gaetano’s Tavern on Main
  • Half Moon Coffee and Grille Cafe

Where to Stay

the Wallingford Victorian Inn

Our romantic, Victorian Inn is the perfect compliment to your relaxing getaway in Wallingford! Each of our luxurious suites at the Wallingford Victorian Inn has everything you need for an indulgent stay. Enjoy fine bath amenities, plush robes, towel warmers, and a private balcony. Included in your stay is a delicious, homemade breakfast each morning and complimentary wine hour every evening at 5:00 p.m. We also offer a range of packages if you’re looking for ways to make your stay extra special!

Plan your Boston to Wallingford, CT, trip now by checking the availability of all our accommodations and booking your stay. When you arrive, we’ll be happy to help you navigate the area and decide how to spend your time!