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Short Weekend Road Trips

Northeast

Boston to Portland, ME 
Follow the Lighthouses to Maine’s Culture Capital

The Route (123 miles)
Avoiding I-95 in favor of Route 1 will take you closer to the coast and let you meander through quaint Maine towns like Ogunquit and Kennebunk. Get the Map

Roadside Attractions
After 70 miles of driving, stop at Maine's Cape Neddick “Nubble” Light, one of the world's most photographed lighthouses, in York, and Portland Head, the state's oldest lighthouse, in Cape Elizabeth, just before you reach Portland. Once in Portland – the state's largest city and its cultural capital – check out attractions like the Portland Museum of Art (Maine's oldest and largest art museum), the Shipyard Brewing Company (with free daily tastings), and whale-watching cruises (offered May-October). Visit on June 9th for the 40th Annual Old Port Festival, featuring live music, arts and crafts, and plenty of delicious local food. Pop up to nearby Freeport for the L.L. Bean flagship store and outlet and the bizarre Desert of Maine.

Stay the Night
An eco-friendly bed-and-breakfast in downtown Portland, the Wild Iris Inn comprises seven unique rooms in an historic home. Rates from $149/night.

Liz Webber

New York City to Woodstock, NY
Sneak Off to a Hippie Hideaway, by Way of Army Headquarters

The Route (111 miles)
The Palisades Parkway and route 9W will take you along scenic overlooks of the Hudson and through Palisades Interstate Park and Bear Mountain State Park, though from there you'll have to take the Thruway to Woodstock in the Catskills. Get the Map

Roadside Attractions
Throughout the summer, the United States Military Academy at West Point offers daily one- and two-hour tours (except during special events or holidays) of sites like the Main Cadet Chapel and Trophy Point (adult tickets $13 or $15). Once you arrive in Woodstock, don't mistake the town with the famous rock festival held in 1969 (that happened in Bethel, an hour-and-a-half drive away). What you will find are the 250-acre, 111-year-old Byrdcliffe Artists Guild art colony and numerous contemporary art galleries, as well as hiking and mountain biking in the Overlook Mountain Wild Forest. If you're still in a rock n' roll mood, pay your respects to the late Levon Helm, the legendary drummer for The Band who regularly held intimate jam sessions at his Woodstock home.

Stay the Night 
The Woodstock Inn on the Millstream is a cozy 18-room B&B set on three acres of woodland within walking distance of the Village Green. Rates from $137/night (book far in advance for weekend stays).

Liz Webber

New York City to Hyde Park, NY
Enjoy Hudson Views, Haunted Towns, and Historic Mansions

The Route (83 miles)
Skip the Thruway for a leisurely drive straight up Route 9, which hugs the east bank of the Hudson most of the way to Hyde Park, providing gorgeous river views. Get the Map

Roadside Attractions
In the legendary Village of Sleepy Hollow, about 30 miles outside the city, watch out for the headless horseman on a visit to Sleepy Hollow Cemetery, where Ichabod Crane creator Washington Irving and industrialist/philanthropist Andrew Carnegie are buried. If there's time, tour John D. Rockefeller's opulent historic home, Kykuit. Hyde Park also has a fair share of famous homes to visit: the Franklin D. Roosevelt National Historic Site and Eleanor Roosevelt National Historic Site, Val-Kill, as well as the Vanderbilt Mansion National Historic Site. You may not be able to afford a private chef like a Rockefeller or a Vanderbilt, but you can get a world-class meal at one of the five award-winning, student-run restaurants at the Culinary Institute of America. Work off the calories from the truffle butter with a guided kayak tour of the Hudson with the River Connection

Stay the Night
Bed down at the Journey Inn, with seven individually decorated rooms and a gourmet breakfast spread (think pomegranate poached pears and tarragon scrambled eggs). Rates from $150/night, two-night minimum stay required on weekend and from May to November.

Liz Webber

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