Home Travel & Tips 7 Picture-Perfect Small Cities & Towns for Your Summer Road Trip

7 Picture-Perfect Small Cities & Towns for Your Summer Road Trip

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Searching for some new sights (and Instagram bragging rights) on your summer road trip? Add one of these small US cities to your route for great eats, beautiful scenery and fun for the whole family. And see our list of the Airbnb Alternatives for accommodation on the way there!

Note that these cities aren’t listed in any particular order– picking a favorite is just too difficult!

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La Pointe, Wisconsin

7 Picture-Perfect Small Cities & Towns for Your Summer Road Trip

Yes, Wisconsin has islands, and La Pointe on Madeline Island is where you want to beeline to this summer. A short ferry ride from Bayfield, you can start your visit off with a free walking tour of the downtown. After a day spent sailing and lounging on the beach, sit down to a farm-to-table meal, or head to the charming mish-mash of a dive bar that is Tom’s Burned Down Cafe. And if hopelessly picturesque restored dairy farms strike your fancy, be sure to look into the multi-day visual and fiber arts workshops at the Madeline Island School for the Arts.

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Holly
Freelancer, digital nomad and passionate traveler who's dedicated to sharing my experiences and expertise to help you travel better.