Fiona Hardcastle and her family drove more than 3,000 miles on a three‑week road trip through New England this autumn, tracing a route from New York City north along the Atlantic coast, across rural Massachusetts, Vermont and New Hampshire, and into Maine’s coastal islands and national park. The journey combined city stops and seaside cottages with mountain drives and national‑park hikes, and the family said the itinerary appealed to teenagers and parents alike.
Hardcastle said favourable exchange rates and discounted off‑season flights helped make the trip viable for a family of five. She and her husband rented a bright orange Jeep Wrangler for the drive, citing its cargo space and rugged profile as useful for long stretches on scenic routes and narrow island roads.
The group flew into New York for a short city stay before heading north. They split time between Moxy Chelsea and Moxy Lower East Side, budget‑friendly hotels from Marriott, and used New York City Passes to visit landmarks including the Rockefeller Center observation deck. From Manhattan they launched the road portion of the trip, driving north to Cape Cod with Bruce Springsteen on the radio and an orange Jeep stuffed with luggage.
On Cape Cod, the family stayed at the Wequassett, a century‑old property of clapboard cottages on 27 acres overlooking Pleasant Bay. They took a private boat shuttle to a small beach and dined at Atlantic 28, where the head chef James Hackney served lobster carbonara. Hyannis provided a more modest base at the Red Jacket resort, which the family used to explore Provincetown’s whale‑watching boats and Provincetown’s LGBTQ scene.
A whale‑watching outing with the Dolphin Fleet produced multiple humpback sightings, and the family took an off‑road sand tour of the dunes operated by Art’s Dune Tours, a family business founded in 1946. From the Cape they took the ferry to Nantucket, where they stayed at The Summer House on Ocean Avenue and used public buses to explore the island’s cottages, bluffs and waterfront paths.
The trip’s itinerary included a mix of high and low‑cost experiences. In Rhode Island, they spent time at the Preserve Sporting Club and Resort, where the family occupied a three‑storey house on the property and tried clay pigeon shooting and golf carts. A stop in the Berkshires provided an overnight break en route to Vermont.
In Vermont the route followed scenic byways: the family drove north through the Mohawk Trail and Route 100 toward Stowe, stopping for a hike and time at The Lodge at Spruce Peak. They peeled back the Jeep’s roof on clear days to take in views of the Green Mountains and Mount Mansfield. The party also visited Bingham Falls and drove through Smugglers Notch, a narrow mountain pass with steep rock walls.
The trip continued into New Hampshire, where the family drove the seven‑mile Mount Washington Auto Road to the summit. Hardcastle described the climb as steep and foggy, with hairpin turns that tested nerves; a souvenir bumper sticker marked their achievement. They later stayed at the Omni Mount Washington Resort, a grand hotel known for hosting the 1944 Bretton Woods conference that led to the creation of the World Bank.
Heading east, the family stopped along the Kancamagus Highway and searched for loons on Lake Winnipesauke before crossing into Maine. Boothbay Harbour provided a rainy welcome and a visit to Gimbel’s country store, where the group purchased lobster‑patterned sweaters. Their base for three nights on Mount Desert Island was The Asticou, a renovated hotel with clapboard cottages overlooking the bay.
From Mount Desert Island they explored Acadia National Park, walking Jordan Pond, visiting Bubble Rock and Thunder Hole, and driving or hiking to the summit of Cadillac Mountain, which is often cited as the first place to see sunrise in the continental United States. The family spent time in Bar Harbor for lunch, shopping and seafood before heading south toward Boston.
The final leg included a walk around Boston Common, a visit to Harvard University and some time on Newbury Street. The trip ended with an evening at Fenway Park for a Red Sox game against the Los Angeles Dodgers; the family purchased baseball caps and recalled the crowd’s electric atmosphere. A minor incident at the game — a bartender asking for identification before serving beer — provided a light final note to the journey.
Hardcastle’s narrative highlighted a mix of activities that may appeal to families: short city stops for museums and observation decks, beach and island time with easy ferry access, guided wildlife excursions such as whale watching, historical hotels and mountain drives, and national park hikes. She also noted practical advantages that helped shape the itinerary: lower fuel prices in the U.S. compared with the U.K., shoulder‑season discounts and quieter tourism in some popular destinations.
The trip covered coastal landscapes, islands, forested mountain roads and small towns known for local food and outdoor recreation. Hardcastle’s account underscored the region’s variety — from the clam shacks of Cape Cod and lobster dinners in Maine to the ski‑resort ambience of Stowe and the grand‑hotel history of the White Mountains — and suggested that a single vehicle and a flexible schedule can accommodate multi‑generation family travel across varied terrain.
Hardcastle and her family said they left the Jeep and their New England route with a collection of memories and mementos, from shell‑strewn beaches to summit bumper stickers, and planned to return with identification in hand for the next stadium beer.