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Two people enjoying drinks on a deck with an ocean view
Beauport Hotel Gloucester

Travel Like a Local

Get off the beaten path and explore the region like a true-blue New Englander. 

Day

1
Porch with chairs and hanging flower baskets
Red Lion Inn

Stockbridge, Massachusetts

Brewery
Cocktails
Museum

Norman Rockwell Museum - America’s iconic painter put his hometown in much of his work and the famous museum showcases that local flavor. 

EAT

Porch Drinks at the Red Lion Inn

End your day with a crafted cocktail on the porch of Stockbridge’s most famous hotel. 

PLAY

Barrington Brewery

Solar power helps power the beer making, while local flavors anchor the menu.

STAY

Red Lion Inn

The lodging options include the historic main inn, the 17-room contemporary guest house, and a turn-of-the-century firehouse. 

Inn at Stockbridge

The beautiful Berkshires region is the stunning backdrop at this inn, whose 15 luxury appointed rooms make their home in a  1906 Georgian style mansion.

Day

2
Closeup view of business entry
MA Office of Tourism

Boston, Massachusetts

City
Dining
Gardens

Visit Fenway Park another time. A real-deal insider’s tour is the only way to truly experience New England’s most celebrated city. 

EAT

Mike’s Pastry vs Modern Pastry

Maybe you can finally settle the local score on who dishes up the best cannoli in Beantown. Better do plenty of research. 

PLAY

Rose Kennedy Greenway

Fountains, art, landscaped gardens and different downtown neighborhoods are all on display during a stroll through this 17-acre park. 

STAY

Boston Yacht Haven Inn & Marina

A 10-room boutique hotel, Boston Yacht serves up stunning water access and Instagram-worthy Boston skyline views.

The Lenox Hotel

After a full day of Boston adventures you’ll appreciate the Lenox’s downtown location and exceptional hospitality.

Day

3
Patio bar with stools and chairs
Hotel Salem

Salem, Massachusetts

City
Cocktails
Museum

Salem Willows Park - Young and old will adore Salem Willows, whose two arcades and waterfront park will keep the family entertained all day long.  

EAT

The Roof at Hotel Salem

Take in the unparalleled Salem sights as you sip down an adult beverage at one of the city's liveliest bars.  

PLAY

Punto Urban Art Museum

Spanning three city blocks, this open-air museum is a showcase of more than 75 grand murals from local and international artists.

STAY

Hawthorne Hotel

Settle into your guest quarters then ask to see the unusual top-floor Sea Captain’s room, which is rich in lore and history.

Hotel Salem

Mid-century flair and an ideal Salem location define the experience at this 44-room boutique hotel. 

Day

4
Harbor with boats

Gloucester, Massachusetts

Beach
City
Lobster

Lobster Boat Tour - The waters of Cape Ann sparkle as you tour one of America’s historic fishing ports. 

EAT

The Lobster Pool

The lobster overfloweth at this acclaimed seafood destination, whose rolls are arguably the North Shore’s best. 

PLAY

Beach Bike Ride from the Beauport Hotel

Beauport’s free bikes are the perfect wheels for exploring Gloucester’s beaches and unmatched seaside views. 

STAY

Beauport Hotel Gloucester

Harkening back to New England’s grand seaside inns of yore, the elegant 94-room Beauport showcases the water from nearly every vantage point.  

Addison Choate

Photo-perfect Rockport is on full display at this cozy retreat only a stone’s throw from the water. 

 

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