Eastern Vermont

The Best Road Trips is a weekly summer series highlighting our favorite getaways from major cities all over the United States.

Some associate Boston with crooked old cobblestone streets, the American Revolution, and clam chowder. (Yum.) And it’s got all that. But those who work and play there know that it’s also filled with sprawling convention centers, progressive universities, and biotech research facilities. A forward-looking town with an eye on the past, Boston combines the charm of a New England harbor town with the mindset of a bustling, modern metropolis. And sometimes, its non-stop vibe can seriously wear a resident out. So if you’re a Bostonian looking for a weekend escape, why not hop in the car and head to a not-too-far destination where you can find some R&R? Get your bags packed and set your GPS: We’ve got some miles to cover.

Road Trip #1: Boston to Kennebunkport, ME

  • Total Driving Time: 1 hour, 42 minutes
  • Distance Covered: 85.4 miles
  • Take This Trip If: You want to bask in the sun like a quality Kennedy or Bush family member would.
Life's a beach.

Life's a beach in luxe Kennebunkport.

A Jonathan Adler-designed guestroom at the Tides Beach Club? Sign us up.

A Jonathan Adler-designed guestroom at the Tides Beach Club? Sign us up.

Enjoy the view from Adirondack chairs at The Colony Hotel.

Enjoy the view from Adirondack chairs at The Colony Hotel.

Originally settled in 1610, Kennebunkport was a small fishing village that experienced an economic boom during the shipbuilding era. But it wasn’t until after the Civil War that Kennebunkport became what it is today: a summer retreat for wealthy families. In fact, former President George W. Bush’s great-grandfather’s compound, Walker’s Point, is located in Kennebunkport, and both he and his father (also former President Bush) have hosted foreign dignitaries at the summer home. What, you may ask, attracts the elite crowds to this Northeastern haven during the summer months? The private-feeling beaches are the area’s main draw and activities such as kayaking, whale-watching, golfing, and fishing are also popular pastimes. If you’re looking for a cozy hotel that’s also spot-on chic, The Tides Beach Club is the perfect choice. Fully renovated in 2011, the hotel’s vibe is South Beach-esque and trendy while maintaining a quaint New England feel. Two suites designed by Jonathan Adler, spectacular ocean views, and a contemporary restaurant with a sophisticated menu are just some of the upgrades that came with the renovation. For a more budget-conscious option, stay at The Colony Hotel. This historic hotel has a welcoming attitude to both kids and dogs, attracting families with its heated saltwater swimming pool and private sandy beach.

  • Top Driving Tip: Don’t forget about all the neighboring areas: Kennebunkport is a great launching point for visiting nearby towns like Ogunquit — known for its long sandy beaches and as being Maine’s biggest LGBT destination — or York, to see the famous Neddick Lighthouse.

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