Highland Square – Akron, OH

A lively community with a slight bohemian flair, Highland Square features a diverse blend of residents with a strong appreciation for art, music, and plurality. Although the origins of the name Highland Square have been lost to history, the neighborhood has a wonderfully rich story to tell. Located about 35 miles south of the center of Cleveland, this dynamic area offers an eclectic selection of businesses. With a little bit of everything, people are drawn to Highland Square to live and visit.

Schools in Highland Square

School data provided by GreatSchools

Restaurants & Nightlife

Most everything you need lies along West Market Street, the main drag also known as State Route 18. A few fast food and chain restaurants reside here, but Highland Square takes pride in its local flavor, especially when it comes to food. Ditch the typical travel breakfast and head to Wally Waffle. Established in 1975, Wally Waffle treats each person to the most delectably fresh, made-from-scratch food all day. Munch heavenly waffles (of course), light and crispy pancakes, eggs, grits, sausage, bacon and just about everything else you’d want for a hearty breakfast, and then wash it all down with your choice of several juices. Amazing burgers, chili cheese fries, and the country-fried chicken round out the menu and keep locals coming back for more. Expect fairly cheap prices and plan on waiting for a table — this place stays packed. Mr. Zub’s Deli's laid-back dive-like atmosphere might not impress you, but the food will. Sandwiches made fresh to order and named after cult movie and entertainment personalities add to the ambiance. Try the Tommy Boy, Lisa Simpson or Rock Balboa, and don’t forget the tater tots everyone raves about. Slow service counteracted by good prices make it worth the wait to eat here. A visit to Angel Falls Coffee Company takes you straight into Highland Square’s living room. Rated the #1 Independent Coffee Establishment in Akron, the warm mood here welcomes you into an incredibly diverse family. Folks like to hang out just to chat and enjoy each other’s company and plug into free Wi-Fi. Limited nightlife choices exist in this neighborhood, but the available options deliver. Square features a loud dance club atmosphere, complete with pool table, bar, big-screen Wii play area, dance floor, lounge room and an outdoor smoking patio. Popular for hosting live DJs, a wide selection of martini’s (try the delicious Cappuccino Martini), and karaoke, this club has been voted one of the 200 Best Gay Bars in the World by OUT Magazine. Friendly and popular with both gay and straight people alike, this club comes with surprisingly little drama for such an in-demand club. For great prices and the largest selection of beer in the area, visit Matinee, which connects to Mr. Zub’s. For a more simple bar experience, Ray’s Pub fits the bill well. Drop in more than a couple of times, and the bartender will remember your name and your favorite drink.

History & Culture

The oldest part of Highland Square, Portage Pass was named after the trail Native Americans made to carry their canoes from one body of water to the next. The area around the path then developed as a residential area for wealthy Akron citizens. Since then, it has grown into a densely populated and very diverse residential community. Live music permeates from area pubs year-round, but The Tangier serves as a cornerstone in area entertainment, in operation since the 1960’s. Famous for hosting stars of the classic rock era, this venue also brings in newer, young talent. Combining art and music, the Highland Square Neighborhood Association presents “Porch Rokr” each year. Designed to bring the community together and celebrate local talent, the tag line states it simply: “Bands on the porch, art on the lawn”. This festival provides tons of fun for both kids and adults.


Transportation choices abound in Highland Square. Choose to drive your own car, take a taxi, bus or trolley, walk or ride a bike. Uber services the area, but most locals get from one place to the other within the community either walking or biking. The fairly compact area means you can slow down a little and enjoy the beauty of the neighborhood. One of the first area neighborhoods with biking lanes, Highland Square posts signs alerting bikers to various paths with distances listed. Use caution when biking along Market Street, though. Traffic gets a little dicey and drivers don’t always look in the bike lane when passing or turning. Call ahead for a cab rather than waiting for an occasional taxi to drive by, but the cheaper buses run often. If you drive your own vehicle, parking is a challenge here. Avoid the parking meters along the main road and drive down side streets for free spots instead. A well-placed free public lot behind Chipotle serves as a central location to almost everything.


Median rent in Highland Square costs $669, just under the average for Cleveland. The Akron city bus takes you to Cleveland for just $5 each way. For beer, most places charge an average of $3 for a glass of domestic, but you can usually get it a dollar cheaper during happy hour. Gas is 5 percent lower than the national average.


Find most of the area shopping options up and down the aptly named Market Street. While you won't find many stores, a few very good ones reside within this location. NEXT, a high-end specialty shoe and clothing store, keeps current with trends and new designer fashions. Although pricey, this establishment features high-quality merchandise and the cultural clothing information provided by the staff provides a nice touch. Clean and modern, it often has good sales to appeal to the more budget-oriented shopper. Two Turtles pet shop has been in the area for a long time and serves as the only neighborhood pet store. Friendly and helpful staff pair you up with a new pet or supplies. In the warmer months, shop the Countryside Farmers Market on the corner of Conger Avenue and Market Street. Enjoy fresh produce grown on various working farms that have a partnership with the Cuyahoga Valley National Park.


No true park system exists within this cozy neighborhood, but a few small green spaces stand ready for your pleasure. Try Teagle Park, a tiny lawn area with a large sculpture by nationally renowned artist, Don Drumm. Relax while your children play at Gale Park, which features a couple of park benches and a simple jungle gym. A little larger, Will Christy Park proffers several park benches and a more elaborate playground for children. These parks welcome everyone, including pets as long as you keep them leashed and picked up after. A section of Market Street practically turns into a park during Akron Square Fest, a fun family event hosted by Highland each year in September. Live entertainment stages, artist exhibits, stilt walkers, street performers, and lots for the kids to do characterize this event. Free parking and trolley service make getting into this event simple.
The Highland Square
733 W Market St, Akron, OH 44303
2 wks
$710 - 1,000 1-2 Bed Available Now
Hampshire House
75 N Portage Path, Akron, OH 44303
2 wks
Call for Rent Studio - 2 Bed Available Soon
2 wks
Highland Towers Apartments
900 W Market St, Akron, OH 44313
$830 - 1,100 1-3 Bed Available Now