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New England itineraries

New England is quite as large a lump of earth as my heart can really take in.
– Nathaniel Hawthorne

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On the Road Trip

U.S. Road Trips: The Northeast

U.S. Road Trips: The Northeast
Coastal Maine. Yuri Long / Flickr

The quintessential city escape: seaside retreats, rolling hills, secluded lakes, beachy hangouts, sunset beers. Pack up and hit the highway with this list of weekend road trip destinations in the northeast United States. Are we there yet?

Jump to: Connecticut | Maine | Maryland | Massachusetts | New York | Vermont


Head to Southport and Westport if you're in the mood for low-key antiquing and the beach. The Delmar Hotel and Artisan restaurant are around the corner from what is, quite possibly, the sweetest, tiniest town. Terrain, Anthropologie's stunning offshoot (greenhouse, garden center, cafe), just opened up in Westport.
Route to take: Straight shot on I-95, 90 minutes from Manhattan.
Good to know: The Gray Goose Cafe is adorable for lunch.

Head to Greenwich if you're in the mood for fresh air and fancy shopping. Hit up "the ave" for boutiques like Dighton Rhode and Privet House. Enjoy a leisurely lunch at local favorite Meli Melo, where specialties include French onion soup and freshly squeezed oj. If you're still around for dinner stroll down to L'Escale for harborside dining and specialty cocktails named for the seven heavenly virtues.
Route to take: One hour by car from New York City via I-95.
Good to know: The Drawing Room serves handed blended teas and delicious scones with clotted cream. Their adjacent shop is the place to buy decorative pillows and scented candles. Stop off in Port Chester for a pizza margarita at Mario Batali's Tarry Lodge and freshly baked bread and cured meats from the market.


Head to Rockland if you're in the mood for farm-fresh food without the Boston or New York price tag. Make a reservation at Primo and enjoy a creative menu that uses produce and animals raised on the property.
Route to take: Route 1 affords beautiful coastal scenery, complete with waves crashing into rocky cliffsides and charming lighthouses.
Good to know: The Farnsworth Art Museum is also located in Rockland, giving you a good dose of culture along with a fantastic meal.

Head down the coast of Maine if you're in the mood for by-the-book prep, nature adventures, and rural farm areas.
Route to take: Skip around from Camden to Rockport to Kennebunkport to Norway.
Good to know: Stay at the Country Inn or The White Barn Inn; stock up on L.L. Bean; let Ducktrap Kayak handle your paddling details.
While in the area: See Little Black Book for Coastal Maine.


Head to the Chesapeake Coast if you're in the mood for a nautical state of mind. Start by gazing at the sailboats from your bedroom window at Inn at Perry Cabin. Get dirty with buckets of peel-and-eat shrimp poured onto tables covered in brown paper by day; clean up for the five-course dinner menu from a Per Se alum at Bartlett Pear Inn.
Route to take: Route 301 is a pleasant alternative to the NJ Turnpike and I-95.
Good to know: The NYT has a list of finger-licking crab shacks that's worth a gander.


Head to the Berkshires if you're in the mood for dance, theater, yoga, Shakespeare, and skinny dipping with mountain as the backdrop.
Route to take: Saw Mill from NYC, Mohawk Trail into North Adams from Boston.
Good to know: Jacob's Pillow, Mass MoCA, Kripalu, and Canyon Ranch are all here.
While in the area: see our Berkshires hot list and itinerary.

Head to Nantucket if you're in the mood for a new flavor profile on one the coast's most historic islands. Do Dupree & Company for provisions, Brick Bistro for brunch, Ventuno for dinner, and Brotherhood of Thieves for a sunset beer. Shack up at White Elephant or Wauwinet.
Route to take: JetBlue flies to the island during summer months.
Good to know: Take the pooch. There's a lot of outdoor living, dog-friendly hotels, and off-leash beaches.


Head to Phoenicia if you're in the mood for agritourism with a Dutch design bent. Try Stony Creek Farm in Walton, where fancy tents with wood-burning stoves are nestled on a working farm. Nightly harvests become dinner.
Route to take: Take 87 and stop in for a tour of Tuthilltown Spirits, the distillery where Hudson Baby Bourbon is made.
Good to know: The culinary cognoscenti of NYC get their prime cuts from Fleisher's Meats; you can pick up breakfast sausages at their full-service butcher shop.
While in the area: check out our Catskills hit list.

Head to Livingston Manor if you're in the mood for a monastic environment. Book a weekend at Dai Bosatsu Zendo, a Japanese Buddhist sanctuary where you can workshop the basics of being — like breathing and being quiet.
Route to take: The Palisades (from NYC) are soothing and scenic.
Good to know: No prior Zen practice necessary. And if you want your alone time with somebody, you can rent a small cottage on the premises.

Head to Hudson if you're in the mood for juxtaposing well-worn Victorian charm with big city comforts and a bit of edginess. Stay at Inn at Hudson, drink a perfectly pulled espresso at Swallow, check out the mini food truck emporium on Warren Street, have killer (local, sustainable, homemade) burger with the works at the retro-fitted '50s diner Grazin', and finish off with a nightcap and live show at Helsinki.
Route to take: Ride Amtrak right into town; zip up from NYC in a car on 87.
Good to know: Check the schedule for happenings at the cathedral-like Basilica Hudson, an old glue factory that's been turned into a performing arts space.
While in the area: see our Hudson Valley hit list. And our weekend itinerary for Hudson.

Head to the North Fork if you're in the mood for large plots of farmland, farmstands, U-picks, and wineries. Book at slow-food hang Red Barn B&B or North Fork Table and Inn.
Route to take: Tiny town centers dot the Main Road (Route 25) and Sound Avenue (Route 48).
Good to know:The Custer Observatory is open every Saturday from dusk to midnight for stargazing.
While in the area: see our North Fork hit list.

Head to Montauk if you're in the mood for an easy, breezy beach weekend. Ruschmeyer's has a retro camp vibe, but the best way to hang is by renting a little something you can call home.
Route to take: Drive very early in the morning or very late at night on 495 to Sunrise Highway to the very end of Montauk Highway (avoid traffic by using GPS to navigate back roads).
Good to know: BYOB seafood shack Duryea's Lobster Deck, Fishbar on the Lake, and the Ditch Witch food truck are musts.
While in the area: see our guide to the Hamptons.


Head to Woodstock if you're in the mood for quintessential Americana combined with a new, LEED-certified spa. Book the grand Woodstock Inn, right in the heart of the most picture-postcard-perfect New England town ever. This place has it all: roaring fireplaces, delicious, homemade ice cream, covered bridges, sleigh rides in season.
Route to take: The Taconic Parkway from NYC. It might be a slightly longer route, but the scenery — and a stop at the old-school Millbrook Diner (3266 Franklin Ave.; +1-845-677-5319) — makes it worth it.
Good to know: Vermont is just a great state. Gorgeous views, good food, and outdoor activities (from cross country skiing to mountain biking) abound.


U.S. Road Trips: The South
U.S. Road Trips: The Midwest
U.S. Road Trips: The West


Have you seen our list of the Most Romantic Hotels in The Northeast?

Special thanks to contributors Devorah Klein Lev-Tov, Christina Ohly, and Ilaria Urbinati.
Photos: Courtesy of White Barn; the burger at Grazin'; courtesy of Ruschmeyer's.

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