Road Trip Season

READY TO UNLOCK the best season of New England? June offers the perfect blend of pleasant weather, and the reemergence of seasonal businesses. Here are five unique day trips within two hours of Boston.

They all promise an unforgettable adventure to one of our region’s lesser-talked-about destinations. Each location is good for all types of day-trippers: couples, families, best friends and groups. Your packing inspiration includes a refillable bottle of water, car snacks, sunglasses, sunscreen, car-friendly phone charger, small notebook and pen, binoculars, camera, picnic blanket, hat and beach chairs. Have fun!

Four Corners, Tiverton, Rhode Island:

Historical Elegance and Charm

(1:20 south of Boston)

Step into the 18th century while visiting the historic town of Four Corners, Tiverton. It’s a beautifully preserved town near the ocean, and it’s on the National Register of Historic Places. There’s a free walking guide you can find online detailing the architectural gems and history of the area. Find boutiques, antique stores and a cheese shop all within walking distance. Check out the sculpture garden at Four Corners Art Center and get lunch at Groundswell Table + Provisions, a Parisian-inspired café with a patio. For those seeking a nature walk, Fort Barton’s trails have great views and Weetamoo Woods has a historic stone bridge. There’s wine nearby! Check out Westport Rivers Vineyard in the town of Westport, Massachusetts. If it’s a warm enough day, you’ll be close to many beaches—pack accordingly!

New Bedford, Massachusetts:

Maritime Legacy and Artsy Vibes

(1:15 south of Boston)

New Bedford’s downtown is charming and rich with maritime heritage. Cobblestone streets, preserved buildings, art murals, diverse restaurants, shops and ocean views—this town will win your heart. Definitely visit the New Bedford Whaling Museum, with rotating exhibits, a huge ship to climb aboard and many stories of the sea. Visit the Allen C. Haskell Public Gardens for the flowers or go to Fort Taber Park for history. Restaurants with vibes: Cisco Brewers Kitchen & Bar, New Beige, No Problemo, Tia Maria’s European Café, or Play Arcade. New Bedford is 25 minutes east of Four Corners—you could potentially visit both spots in one day!

Portland, Maine:

Coastal Haven for Food and Culture

(2 hours north of Boston)

Portland’s reputation as a culinary destination is well earned. The historic Old Port district is iconic, with cobblestone streets and an eclectic mix of restaurants, breweries and boutiques. You’ll start your day at the Portland Head Light before treating yourself to Maine lobster. It’s the best! Go to Highroller Lobster Co. if you like different sauces or make a reservation at Eventide for the raw bar. Dessert is a doughnut. Get a Holy Donut to go and take it to the Eastern Promenade to enjoy it with a view of Casco Bay.

Activity options: Take a ferry ride to the Casco Bay islands, tour the town atop an old fire engine, or visit the Portland Museum of Art or the Children’s Museum.

Lincoln, Massachusetts:

Farms, Historic Homes, and Ponyhenge

(30 minutes west of Boston)

Escape to Lincoln for rural charm and fun on the farm(s). Explore the deCordova Sculpture Park and Museum, where art and nature merge. Pack a picnic to bring here or simply wander and connect. Schedule a tour at the Gropius House or Codman Estate—both offer a unique story and hold design history. Flower lovers: Wisteria blooms in late May and early June in the Codman Estate’s garden. Enjoy lunch at Verrill Farm, technically in Concord but very close and so good.

For a quirky detour, go to Ponyhenge, a whimsical collection of rocking horses. Visit Mass Audubon’s Drumlin Farm to see the animals or Codman Community Farms for the farm stand. If it’s not dark, stop at Wilson Farm in Lexington for tulip picking on your way home.

Monadnock Region, New Hampshire:

An Outdoor Enthusiast’s Paradise

(1:45 northwest of Boston)

Mount Monadnock is the best hike close to Boston, offering breathtaking, panoramic views at the summit. On a clear day, you can see the city in the distance. There are many trails ranging from 4 to 6 miles, all rated hard in difficulty. For a gentler experience, try Ted’s Trail at Wapack National Wildlife Refuge; it’s 5 miles and rated moderate. There’s also a beautiful walk around the Ponemah Bog that’s rated easy and is less than 1 mile. Take a scenic drive to a quaint town nearby and stop into whatever antique store you pass on the way—there are many! Endless Treasures in Jaffrey is massive. Visit Keene for the breweries and shopping or go to Peterborough for the Bagel Mill. For wine lovers, stop at Fulchino Vineyard in Hollis; there’s outdoor seating, and it’s on the route back to Boston.