Urban Escapes

Five drivable cities where adventure and excitement await

By Sarah Grace Smith / Story Design by Tori Smith

As the days begin to last longer into evenings and the heat starts to rise, many of us are itching to get out of town. Sadly, typical vacation destinations like Florida and Carolina beaches tend to be far and costly.

Lucky for you, we compiled a list of cities just a couple hours away—perfect for a weekend getaway or even a longer stay.

Cincinnati, Ohio

Resting on the border between Ohio and Kentucky, Cincinnati boasts a culture of Midwest kindness and Southern charisma. Known for its food, arts and sports, Cincinnati includes something for everyone.

Animal lovers can visit the city’s famous Fiona the hippo at the Cincinnati Zoo & Botanical Garden. Sports fans can cheer on the Reds, Bengals or Orange and Blue. Foodies can sample Cincinnati chili (it’s on spaghetti!), and beer connoisseurs can visit one of the eighty breweries.

The city also enjoys a wide variety of excellent coffee shops and thought-provoking museums as well as a vibrant music and arts scene.

Holland, Michigan

Named one of “America’s Prettiest Towns” by Forbes Magazine, Holland holds both the charm of a rural getaway and the liveliness of an urban escape. A well-preserved historical Dutch town, Holland gives you a taste of history with its tulip gardens, settlers houses and windmills.

Downtown, you can visit over 100 local shops, galleries, restaurants, and pubs. If you stay during the week, you may even catch a street performance on Thursday night!

Not only does Holland advertise a historical village and a downtown, but it also lies near a few beaches! Most are near hiking trails as well, so you can stay active while you travel.

Louisville, Kentucky

Head on down to the nation’s Bourbon city and experience a town shaped by spirit. Check out both the Urban Bourbon Experience and the Urban Bourbon Trail to take your taste buds on an adventure. The city boasts ten distilleries, thirty-five bars, and more than sixty types of bourbons.

Time flies by at the Churchill Downs racehorse track and the Kentucky Derby Museum, two iconic institutions that showcase Kentucky’s famous thoroughbred horses. Just don’t lose too much money on horse racing.

On the arts side, Louisville happens to be one of the few U.S. cities with a professional orchestra, ballet, opera, dinner theatre, children’s theatre, and Broadway Series. They just can’t get enough!

Chicago, Illinois

The famous Chi town—where else can you devour deep dish, gaze above skyscrapers, and paddle across a lake all in the same day?

From the Magnificent Mile and the Art Institute to the Cubs and the GreenMill Jazz Club, Chicago has a must-see for everyone. It’s no secret why Condé Nast Traveler voted Chicago the Best Big City in the U.S. for six years straight.

Any Chicago explorer worth their salt uses the Chicago CityPASS, a ticket that allows you to visit five main attractions of your choosing within a nine day trip. Options include Shedd Aquarium, Skydeck Chicago, Adler Planetarium, Field Museum and more.

Pittsburgh, Pennsylvania

A city of three rivers, Pittsburgh is the perfect destination for walks along the water and bike rides across the bridges. Head down to Pittsburgh for their sports and festival season or for a chance to return to the outdoors—the city has both!

Home to the famous Andy Warhol Museum, the city prides itself on its numerous art galleries and museums. Craving a sweet treat? Stop by the famed Milkshake Factory, the premium dessert restaurant of Pittsburgh, serving only the best farm fresh dairy.

Be sure to ride the iconic inclines, little red and yellow railway cars that were built in the 1870s. You can now purchase a ticket to rise the natural slopes and view the city skyline.

Cleveland, Ohio

Last but not least, “the Land” offers a quick and convenient weekend getaway. Make your way up north for some kayaking, sunbathing, rock-n-rollin’ and sightseeing.

Over 100 ethnicities comprise the Cleveland population, making it a unique city where cultures and stories weave together. Experience all the culture has to offer through the food, architecture and festivals throughout the city.

Be sure to hit all the main attractions as well. Start by visiting the Rock & Roll Hall of Fame then grab some grub at the West Side Market. End the evening with a night on the town or a game to the Cavs, and you’re set.