The Ultimate New England Road Trip

Contributed By Barrett Hollo

Pack up your favorite boat shoes and grab your L.L. Bean weekender, because a New England road trip has your name all over it.

For East Coasters, options abound when it comes to a road trip. But for ultimate Americana nostalgia, few routes compare to winding from coastal Rhode Island to Maine. From Ocean House‘s expansive private, white-sand beach to a freshly caught seafood feast at Chatham Bars Inn, we’ve rounded up five of our favorite New England getaways, each easily combinable on a road trip.

Ocean House

Watch Hill, Rhode Island

With sweeping ocean views and a timeless elegance that evokes the ambiance of idyllic summers, the Ocean House in Rhode Island makes for a dreamy start to your New England road trip getaway. This boutique, luxury hotel with resort-like amenities is situated right on the beach and offers the highest level of service throughout the property and its forty-nine newly remodeled rooms and 18 suites. These spacious accommodations are each richly appointed to reflect the feel of a sprawling seaside estate, offering an unrivaled residential experience.

In the summertime, make sure you arrive early on Fridays so as not to miss the good, old-fashioned New England lobster boil on the beach, complete with a live band. We also love starting the evening with a glass of Veuve at the property’s Secret Garden champagne bar endorsed by Town & Country, Perks & Corks as well as Malted Barley. Other spots not to miss for a bite include Olympia Tea Room—recognized by Vanity Fair as being “famous not fancy“—as well as Ellas and Cooked Goose.

Vanderbilt, Auberge Collection

Newport, Rhode Island

Originally built by Alfred Gwynne Vanderbilt, a scion of the wealthy Vanderbilt family, this property dates back to 1909 as a vintage Newport mansion that has been restored to its former glory. In fact, it’s one of the few private homes of the era to open its doors to welcome guests. Located right on the waterfront, The Vanderbilt is easily one of Newport’s best-kept secrets. Plus, with only thirty-three rooms and luxury suites, it’s perfectly private.

Should you want to get your legs moving, Vanderbilt is ideally situated to get out and explore – the 3.5-mile walk along the Newport Cliffs allows for the opportunity to see the town’s famous mansions. For some shopping, we recommend checking out Shore Soap Company and Thames Glass. And once you’ve worked up an appetite, a bite at The Mooring is hit the spot. Or, there’s the hotel’s signature restaurant, The Vanderbilt Grill, a sumptuous restaurant where the best local ingredients are on offer in imaginative menus which change throughout the year. For cocktails, check out Fluke and finish up at Dockside for some nightlife.

Chatham Bars Inn

Chatham, Massachusetts

Cape Cod has long been one of New England’s most honored and historic getaways, encompassing 17th-century towns and the spectacular Cape Cod National Seashore. Chatham Bars Inn is our favorite property in the region as it occupies twenty-five acres of beautifully landscaped grounds and sandy ocean beaches, giving you the ultimate peace of mind. Decades back, guests splashed in the surf, played golf in the tangy sea air, took afternoon tea on the wide veranda overlooking panoramic ocean vistas, and dined on the best New England cuisine, featuring fresh-from-the-ocean seafood. Today, you can enjoy the resort lifestyle as so many did, so long ago, at Chatham Bars Inn, lovingly restored to its original grandeur, yet completely updated with the latest amenities.

When you’re ready for an adventure, there are options abound. The property has a fleet of boats for sportfishing, sailing, and day trips to Nantucket Island. No matter if you choose to relax or take up one of the activities, you’ll be sure to feel the quintessential New England vibe. If you’d like to get off property, we adore Chatham Wine Bar and The Squire for cocktails before heading to dinner at Bluefin Sushi & Sake Bar.

Cliff House Maine

Cape Neddick, Maine

Conveniently located in Southern Maine between Ogunquit and York, your New England road trip will take you an hour’s drive north of Boston and a forty-minute drive from Portland. Cliff House is one of the most captivating oceanfront destinations of its kind after a landmark transformation. The property is set on the edge of the Atlantic on the rocky coast of Southern Maine with year-round activities. Cliff House offers panoramic ocean and coastal views from over 130 stylish rooms and suites. The hotel is also just a short distance from Rachel Carson National Wildlife Refuge, one of the country’s largest.

Guests will have no trouble staying entertained and active at Cliff House Maine. In addition to having countless wonderful spots to simply relax and enjoy the remarkable ocean views, they also have many options for those who crave a more engaging experience. Amenities include indoor and outdoor swimming pools, a beautiful luxury spa, and access to the challenging course at the adjacent Cape Neddick Golf Club. Be sure to stop at Walkers, the ultimate stop for a bite, or The Front Porch for cocktails.

White Barn Inn, Auberge Collection

Kennebunkport, Maine

Located in the beautiful coastal town of Kennebunkport, your New England road trip culminates in a stay at White Barn Inn. This staple has been a beloved local landmark for over 150 years, synonymous with warm New England hospitality, rustic charm, and uncompromising attention to detail. Just a ninety-minute drive north of Boston, this inviting property is renowned as one of the country’s most distinctive getaways. The twenty-six-room inn is super cozy, offering guests supreme levels of quality, luxury, and service. Beyond our favorite waterfront cottages, there is a swimming pool and convenient access to fine shopping and art galleries in the charming coastal town of Kennebunkport.

Ocean and Earth at Hidden Pond are your go-tos for a bite off of the property, while we love Old Vines Wine Bar or 50 Local for a drink. But, for the best-kept secret, be sure to check out Little Barn for farm-to-table delights. For a fine dining experience, The White Barn Restaurant has both a AAA Five Diamond and Forbes Five Star endorsement to satisfy the ultimate foodie. Try the 9-course chef’s tasting menu for a true culinary experience!