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The best food-filled road trip from Boston

This customized foodie road trip from Boston packs in a cornucopia of culinary highlights

Written by
Eric Grossman

It doesn't get much better than food and travel—why not combine the two and take a food-focused road trip? Here's a go-to itinerary for anyone looking to take in the area's best treats and culinary experiences. Given New England's relatively small footprint, you can mix and match these stops based on your liking. Just remember to enlist the aid of someone you trust who can cover designated driver duties. If food's not your thing, you can still escape the city in style with one of the best day trips from Boston, or take in one of the best hikes or best beaches near Boston.

RECOMMENDED: Full guide to the best things to do in Boston

The definitive food-filled road trip from Boston

The North Shore

Start off heading towards the North Shore, which contains a multitude of worthy foodie destinations within an hour of the city.

In spooky Salem, eat like a local at Ledger or Bambolina, or nerd out with old school arcade games and pinball machines at Bit Bar, housed in the site of the Old Salem Jail.

Over in tony Newburyport, relax with excellent cocktails and fine pizzas at The Poynt, dine on classic seafood at Michael’s Harborside, or nosh on grass-fed beef and tasty veggie dishes at Superfine Foods. About a mile away, the Newburyport Brewing Company offers a friendly tap room and beer garden. Newburyport includes part of neighboring, sedate Plum Island, a barrier island overlooking salt marshes. Opt for a deck seat at sunset at the Plum Island Grille.

Portland, Maine

Continue on to Maine's largest city—around a two hour drive north of Boston—which attracts a steady stream of foodies from around the country. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares and quaint pubs and dimly lit cocktail bars, like the excellent Blyth & Burrows, which combines the best in innovative mixology and pairs it with equally scrumptious small plates, are set along cobble stoned lanes.

The food scene lives up to the hype: Dine at Evo Kitchen + Bar for progressive twists on Mediterranean cooking, and Union, a vibrant local-centric foodie haunt in The Press Hotel, set in the former home of the Portland Press Herald, the state’s largest newspaper. Spend the night at the hotel, then start the day in style at the city's best coffee spot, Tandem Coffee Roasters.


The Berkshires

Stop through Western Mass, home to the Berkshires. Just off I-90, Stockbridge is the gateway to this beautiful region, part of the Taconic Mountains. Main Street is wonderfully dominated by the venerable Red Lion Inn, a onetime frontier town tavern that still maintains a rousing bar, plus a casual eatery and a gorgeously original dining room with progressive locavore, seasonal food.

Nature and art dominate this area, meaning you can enjoy some nice breaks in between foodie stops. Head over to South Deerfield to visit the Berkshire Brewing Company, New England's oldest regional craft brewery, dating back to 1994. To get the kind of farm-to-table experience the region is known for, make the drive to charming Williamstown, where Mezze Bistro & Bar specializes in locally-sourced small plates, craft cocktails and boutique wines.

Newport, R.I.

It doesn't get much more scenic, and tasty, than Newport. Take the Cliff Walk, which has stunning views over the ocean, or relax at the public Easton’s Beach. Stroll past cool shops and eateries on narrow Thames Street. On Marlborough Street, dine at the White Horse Tavern, which claims to be America’s oldest restaurant. Near the harbor, Bowen’s Wharf’s harbor buildings date back to the 1700s and today offer an inviting maze of restaurants and shops. Stroll over the causeway to Goat Island where the Newport Harbor Lighthouse is overlooked by the upscale Gurney’s Resort. Spend the night there and enjoy dinner at the hotel's excellent Scarpetta, or eat al fresco at The Pineapple Club.

Need to walk off all those eats? The Newport mansions of the Gilded Age still impress, and that’s what they were built to do. (If you have time for only one, check out The Breakers.) Near the International Tennis Hall of Fame, theAudrain Auto Museum houses a seasonally rotating display of impressive cars inside a gorgeous Art Deco building.


Providence, R.I.

Just a short drive south of Boston, Providence is a food lover’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales Universitys College of Culinary Arts is a major factor.

Hemenway’s in downtown is the grand dame of area seafood restaurants; and Waterman Grille is a hidden jewel on the East Side near Brown University. Federal Hill, the city’s impressive Italian neighborhood, is loaded with Italian eateries and shops. Yoleni’s is a multi-purpose culinary concept with 40,000 square feet of Greek goodies.

Waterplace Park is a lovely gathering spot, and it anchors the city’s annual WaterFire program, which runs from spring through late fall; braziers along the Providence River are lit at sunset and stoked with aromatic wood by black-clad figures on boats, while themed music plays. Bring some snacks and unwind with this unique experience.

Cape Cod

To many locals, when it comes to stomach space, all roads lead to the Cape.

Despite being lined with great beaches, cool boutiques, and relaxing spots to eat and drink, Falmouth is one of the Cape’s least touristy towns. Do breakfast or lunch like a local at The Pickle Jar, and the Bear in Boots gastropub has craft beers, great food, and fun events.

Creative, sassy P-town — only a 90-minute ferry ride from Boston — is an artsy LGBT hot spot; it’s got a great mix of galleries showing nautical scenes and nightclubs doing fun cabarets. Lined with dozens of colorful shops, friendly eateries and local businesses, Commercial Street is the bustling heart of the town. Seek out one of the many events and festivals that fuel the thriving arts scene.

The famous Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats from the sea. Climb the 252-ft. granite Pilgrim Monument for dramatic harbor views, then escape to Race Point Beach to enjoy the sights, sounds and smells of the open ocean.

Eat innovative seasonal dishes at the suave Sage Inn’s lounge and great seafood at Mac’s Fish House, which has crispy fish and chips and Happy Hour buck oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore, including Truro’s picturesque Highland Light. (Truro is also home to the fun, fertile Truro Vineyards and South Hollow Spirits.)

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