Our Stunning New England Road Trip!!
New England Road Trip – 12 days:
This 12 night Road Trip takes in a circular route from Boston, whilst beautiful at any time of year, the Autumn (Fall) colours of September / October are ideal.
Night 1, 2 & 3: Boston
Your New England adventure begins in Boston, a city where colonial history and modern energy coexist effortlessly. Wander the Freedom Trail, a 2.5‑mile path linking iconic sites like the Old State House, Paul Revere’s House, and Faneuil Hall. The walk gives you a sense of the city’s revolutionary roots while weaving through lively neighbourhoods. For lunch, head to the North End, Boston’s Little Italy, where you can tuck into handmade pasta at Giacomo’s or wood‑fired pizza at Regina Pizzeria. Don’t leave without a cannoli from Mike’s Pastry or Modern Pastry, locals debate endlessly which is better.
Explore Boston Public Garden, perhaps taking a swan boat ride if the season allows. As evening falls, grab a drink at Trillium Brewing Company, known for its hazy IPAs, or enjoy oysters and cocktails at Row 34 in the Seaport. Boston’s food scene is sophisticated but unpretentious, and it sets the tone for the journey ahead.
Night 4: The Berkshires
Leaving the city behind, drive west toward The Berkshires, a region of rolling hills, farm‑to‑table dining, and world‑class arts. Base yourself in towns like Lenox, Great Barrington, or Stockbridge, each with its own charm. Spend a morning at The Mount, Edith Wharton’s elegant estate, where the gardens and architecture feel like stepping into a novel. Art lovers shouldn’t miss MASS MoCA in North Adams, one of the largest contemporary art museums in the country, housed in a sprawling converted factory complex.
Night 5 & 6: Stowe
Next, head north into Vermont, where the landscape becomes greener and more pastoral as you approach Stowe. This mountain town is postcard‑perfect, with covered bridges, winding roads, and the dramatic silhouette of Mount Mansfield. Start with a visit to Smugglers’ Notch, a narrow mountain pass with towering cliffs and scenic pull‑offs. If you enjoy hiking, the Stowe Pinnacle Trail rewards you with sweeping valley views.
Stowe is also a haven for food and drink. Stop at the Cold Hollow Cider Mill for fresh cider donuts, then visit The Alchemist Brewery, home of the legendary Heady Topper IPA. For dinner, Harrison’s offers cozy New England fare, while Plate serves creative, modern dishes. Before leaving town, take a tour of the Ben & Jerry’s Factory in nearby Waterbury, it’s touristy, but undeniably fun.
Night 7 & 8: Jackson
From Stowe, cross into New Hampshire’s White Mountains and settle in Jackson, a charming village known for its covered bridge, scenic vistas, and outdoor adventures. The drive itself is spectacular, especially if you take the Kancamagus Highway, one of New England’s most beautiful routes. In Jackson, explore Jackson Falls, a series of gentle cascades perfect for a picnic or a refreshing dip. If you’re feeling adventurous, ride the Mount Washington Auto Road or take the cog railway to the summit for dramatic views across the Presidential Range.
For dining, The Thompson House Eatery is a standout, offering farm‑driven cuisine in an intimate setting. For something more casual, Red Fox Bar & Grille serves hearty comfort food and wood‑fired pizzas. End your evening with a drink at Wildcat Inn & Tavern, a classic New England spot with live music and a welcoming atmosphere.
Night 9 &10: Acadia NP
Your journey then turns east toward the rugged coast of Maine and the breathtaking landscapes of Acadia National Park. Base yourself in Bar Harbor, a lively seaside town with shops, cafés, and waterfront views. Spend your days exploring Acadia’s highlights: drive the Park Loop Road, hike the Beehive Trail if you’re up for a challenge, or enjoy the gentler Ocean Path from Sand Beach to Otter Point. Sunrise from Cadillac Mountain is a bucket‑list moment, one of the first places in the U.S. to see the sun at certain times of year.
Bar Harbor’s food scene is all about fresh seafood. Enjoy a classic lobster roll at Thurston’s Lobster Pound, or try elevated coastal cuisine at Havana or Galyn’s. For drinks, Atlantic Brewing Company offers tastings of local ales, while Project Social serves excellent cocktails and small plates.
Night 11 & 12: Salem
As your trip winds down, drive south to Salem, a town where maritime history and witch‑trial lore intertwine. Visit the Peabody Essex Museum, one of the oldest continuously operating museums in the country, and explore the Salem Witch Museum or Witch House for a deeper look at the infamous 1692 trials. Wander the cobblestone streets, browse quirky shops, and enjoy the harbour views.
For food, Ledger Restaurant & Bar serves inventive dishes in a historic bank building, while Turner’s Seafood offers some of the freshest catches in town. Grab a final drink at Notch Brewing, known for its crisp, European‑style lagers, and toast to a road trip filled with culture, nature, and unforgettable flavours.
Please use this itinerary as a guide. We truly love creating bespoke road trips and enjoy nothing more than discussing all options with you before pulling it all together in your own personalised itinerary!
It’s so easy to get started, simply give us a call, click on the enquiry button or book a consultation to design your dream trip!
