20 Jul 6 Charming Road Trips Through New England
Andrea McHugh, Broadry
Whether it’s white church steeples craning above the New England treetops, the wide, windswept beaches of the mid-Atlantic, or the quiet charm of the Southern coast, there’s a whole lot of summer left to explore some lesser-known coastal enclaves that should be on your summer travel itinerary.
Watch Hill, Rhode Island
Not far from Newport, its notable neighbor to the north, Watch Hill has a decidedly quieter vibe with a tiny “downtown” – a single strip – peppered with just a handful of boutiques, casual eateries and ice cream shops. Little ones delight in a visit to the Flying Horses Carousel, the oldest continuously operating merry-go-round in the country.
Around town, tall hedges surround perfectly manicured estates, commanding privacy which is especially favored by celebrity residents like pop star Taylor Swift, who chose a $17.75 million mansion built in the 1930s on the highest point in the village for her summertime playground.
Talk of Watch Hill is incomplete without highlighting the Ocean House, a meticulously and luxuriously reconstructed Relais & Châteaux property perched on the bluffs overlooking the cerulean waves of the Atlantic. The gorgeous beach here is kid-friendly with Lilly Pulitzer-style cabanas and comfortable lounge chairs, boogie boards, and sandcastle gear available.
Here opulent vehicles are de rigueur, so only the most exceptional turn heads, like the 2021 Aston Martin DBX, the luxury automaker’s first SUV with a twin-turbo V-8 engine that purrs. The panoramic sunroof, buttery soft leather and unmatched styling, helps, and selfies with this gem of a vehicle are commonplace.
To escape Watch Hill’s more bustling nooks, head to nearby Napatree Point, a long sandy spit that juts out into the sea, marking the southernmost point of mainland Rhode Island and the perfect spot for the ‘gram.
Chebeague Island, Maine
Just 10 nautical miles off the seaport city of Portland – arguably New England culinary hotbed – Chebeague is the largest of the famed Casco Bay Islands. It boasts a quintessentially Maine landscape, complete with a rocky shoreline, lush green tree canopies and water temperatures with a little bite.
Chebeague (pronounced “shuh big”) provided fertile fishing ground for the Native Americans who settled this island, which today, is home to generations of year-round and summer residents. Some of these families date back to the island’s Colonial Era economic heyday when Chebeague became known for its “stone sloopers;” men who carried ballast and stone from local quarries to stabilize 19th-century sailing ships.
The best way to explore this postcard-perfect island is by bike (The Bikeman offers free bike loans) so you can take your time, snap countless pics and roll up to a clam shack to score a buttery lobster roll.
Old Greenwich, Connecticut
While Greenwich is one of the best-known places in all of Connecticut, particularly as one of the country’s wealthiest enclaves, it’s Old Greenwich, a lesser known part of town, that emanates that classic New England beach town charm one won’t soon forget.
Tucked into the southeastern corner of the state overlooking the serenity of the Long Island Sound, Old Greenwich is peppered with century-old Victorian homes where the less than 9,000 residents often sip their morning coffee on wrap-around porches — through a modern palatial mansion or two isn’t particularly uncommon.
As the coastal community sits on a small swath of land that juts out into the sound, cool breezes that glide across the brackish water are a welcome escape for summer’s heart further inland. Head “downtown” for some relaxing shopping, coffee cafes, delightful bistros and even some critically acclaimed restaurants. In true Rockwellian spirit, the annual Memorial Day Parade brings out the whole town, and Fourth of July fireworks are a must.
South Hero, Vermont
Vermont’s captivating Champlain Islands are an outdoor enthusiast’s wonderland and idyllic for soaking up the spoils of summer. Hiking, biking, boating, fishing, kayaking, standup paddleboarding and camping are plentiful throughout this archipelago that comes close to the Canadian border.
At just over 30 square miles, South Hero Island, also known as Grand Isle, is the largest island in Lake Champlain. It’s connected to another island, North Hero, by Vermont’s only drawbridge and is home to Grand Isle State Park, which at 226-acres, is the most popular campground in the state.
This time of year, it’s also one of the most alluring, with swaths of wildflowers in bloom, and the essence of local flavor comes alive on the palate at local vineyards and farms. A popular music series at Snow Farm Vineyard is a seasonal staple, with folks flocking from far and wide to listen to tunes, toss their shoes and dance by the vines. By fall, harvest season arrives in full swing and the apples are plentiful. Go on an apple picking adventure at Hackett Orchard, home to nearly 50 varieties, and after, sink your teeth into some warm cider donuts and hot apple cider.
With more than 1,500 miles of coastline, The Bay State is home countless idyllic summer respites along the sea. While Cape Cod, Nantucket and Martha’s Vineyard continually grab headlines — and boasts the seasonal crowds to show for it — the historic seaport of Newburyport beautifully blends small-town charm with the busyness of a thriving destination.
Evidence of its past as a Colonial Era shipping center, and later a shipbuilding mecca, manifests in the many historic buildings and homes throughout town, each with unique head-turning architecture. The Custom House Marine Museum on the waterfront is housed in a Greek Revival dating back to 1835 overlooking the scenic Merrimack River and is home to an array of maritime treasures and artifacts.
Downtown Newburyport, which is delightfully walkable with something to see around every corner, is peppered with shops, bookstores, restaurants and plenty for families to enjoy. But to unplug and truly enjoy the spoils of this corner of the world, head outside of the city center to Plum Island, a barrier island just off the coast that is 11 miles of unspoiled coastal terrain. Named for the picturesque beach plum shrubs that grow in the dunes, Plum Island has ample acreage to jump in the crashing surf, explore small quiet beaches, kayak, fish, boat or even enjoy bird watching at Parker River National Wildlife Refuge.
Portsmouth, New Hampshire
The Granite State is home to just 13 miles of coastline — the shortest in all of the coastal U.S. — but this tiny stretch is worth seeking out. The city of Portsmouth anchors what’s referred to most often as the Seacoast Region and sits near the mouth of the Piscataqua River which acts as the New Hampshire Maine border.
For one of the most quintessential New England views, head to the historic Portsmouth Harbor Light, which has served as a navigational beacon since 1877 — and still does. It’s worth climbing the 44 stairs and 7-rung ladder to the lantern room to garner some of the very best panoramic coastal views you’ll see anywhere.
A vital shipbuilding port that pre-dates the American Revolution, Portsmouth’s quaint cobblestone street offers a glimpse of the city’s past while Market Square has been the charming commercial center since the 17th century.
Hampton Beach is a longtime family favorite but can draw crowds with its bustling boardwalk, ice cream parlors and ample souvenir shops. If you’d rather skip the masses and seek more serene shores, head to Great Island Common, just 10 minutes outside the city. It’s perfect for waterfront picnics, a refreshing dip, and more than 30 acres of greenspace to wander.