Adventures Along Ohio’s Winding Road


A special thanks to Ohio’s Winding Road and Ohio. Find It Here. for sponsoring this post!

Looking for thrilling outdoor adventures, historical towns, picturesque landscapes, local flavors and welcoming communities? Then you need to adventure along Ohio’s Winding Road to escape from the hustle and bustle of everyday life and seek the peaceful scenery of southeastern Ohio!

Looking for more things to do in Southeast Ohio? Read these Southeast Ohio Travel Guides

Where is Ohio’s Winding Road?

Ohio’s Winding Road represents the Appalachian region of Ohio, which consists of nine counties- Athens, Fairfield, Hocking, Meigs, Morgan, Muskingum, Perry, Vinton and Washington. This Southeast Ohio region is defined by the Hocking and Muskingum River Valleys and microregions like the Little Cities of Black Diamonds.

Outdoor Adventures Along Ohio’s Winding Road

This region of Southeast Ohio boasts breathtaking rugged landscapes awaiting to be explored. Nature enthusiasts and outdoor adventure seekers will find plenty of thrilling things to do along Ohio’s Winding Road.

Baileys Trail System

With 26 miles currently available and a total of 88 miles planned, the Baileys Trail System is built for all skill levels of cyclists, hikers and runners. Trails lead you through some of the Appalachian region’s best landscapes, including the Wayne National Forest. There are two trailheads located at Chauncey-Dover Park in Millfield and Doanville-York near Nelsonville, and trails range from gravel surfaces to natural rugged terrain surfaces.

Tecumseh Lake Loop Trail

Located near Shawnee, in the Wayne National Forest, Tecumseh Lake sits on the site of the Double X Mine. The Tecumseh Lake Loop Trail is a short 0.5-mile loop hike around the lake. This trail and the 2.5-mile Wood Thrush Trail is part of the Buckeye Trail (a 1440+ mile trail that winds around Ohio).

We opted to hike the short 0.5-mile lake loop. It was a peaceful hike around the lake with great water views and natural trails through lush woods.

Robinson’s Cave

Located in New Straitsville, Robinson’s Cave is an important site for the United States’ labor history. This 1000-square foot natural cave once was the secret location for disgruntled mine workers in the 1880’s, here the miners secretly met and formed the United Mine Workers of America union. Later the cave became a gathering place for locals with a wooden carousel and a ten-pin bowling alley, now visitors can take a short hike to view the cave in its natural state.

Burr Oak State Park

With nearly 2,600-acres, Burr Oak State Park is a nature enthusiast’s dream. Located in the foothills of the Appalachians, the surrounding landscape features woodlands, forested ridges and hollows. Visitors can hike along miles of trails, camp, fish, swim and boat in the 664-acre Burr Oak Lake.

We rented a pontoon boat and enjoyed a few quiet hours on the lake. Surrounded by lush trees, the lake is home to several Bald Eagles which you might catch a glance of while they fish in the lake and nest in the surrounding trees.

More outdoor adventures along Ohio’s Winding Road: bird watching along the Ora Anderson Trail, Boch Hollow Nature Preserve, Wayne National Forest, Zaleski State Forest, bridle trails, miles of ATV, UTV and dirt bike trails, and miles of paved roads perfect for scenic motorcycle rides.

More Things To Do In Southeast Ohio

Explore the Little Cities of Black Diamonds

Dozens of small towns dot Ohio’s Appalachian foothills, collectively, these towns are named the Little Cities of Black Diamonds. These former coal mining communities are building a new future for themselves by revitalizing the town facades while preserving their historic past. Take some time to explore the towns, support local businesses and learn about the history of these unique Ohio towns.

Explore Nelsonville

Located near Wayne National Forest and Hocking Hills State Park, Nelsonville is a great starting point for your southeast Ohio adventures. Be sure to visit Fullbrooks Café, Rocky Boots Outlet and Boot Factory Grill, stroll around the Historic Square Art District, admire the historic star brick sidewalks, watch a show at Stuart’s Opera House and catch a ride on a historic train along the Hocking Valley Scenic Railway.

Explore Shawnee

Nestled in the heart of the Wayne National Forest, Shawnee is a small Ohio town on the brink of revitalization. This once lively mining town now quietly awaits visitors to explore its historic streets, admire historic buildings, visit Ohio’s Winding Road Marketplace, take a walking tour of Shawnee and the historic Tecumseh Theater, dine and drink at the Black Diamond Tavern and take a moment to appreciate the coal mining history and Coal Miner Statue which was sculpted by Ohio artist Alan Cottrill. Once you’ve explored Shawnee, be sure to experience Shawnee’s 20 Under 20 (20 destinations under 20 miles).

Payne Cemetery

This historic cemetery is the only remnant of a freed African American community known as Paynes Crossing. Ongoing research indicated that Paynes Crossing may have been established specifically for the Underground Railroad.

Big Muskie Bucket

Once the world’s largest earth moving machine, Big Muskie could move 39 million pounds of earth every hour! The machine was destroyed in 1999 and now just the bucket remains as a reminder of Southeast Ohio’s mining past.

More historical stops along Ohio’s Winding Road: Buffington Island State Park, The John & Annie Glenn Museum, numerous historical societies and museums and historic covered bridges and round barns.

Where to Stay Along Ohio’s Winding Road

Located in Chesterhill, the Milk House Cottage welcomes guests to a quiet retreat after a long day exploring Ohio’s Winding Road. As one of the cutest Airbnb’s I’ve ever stayed in, this small cottage sits on the remnants of the property’s milk house right next to the original dairy farm’s silo.

With all the comforts of home, a private patio, enchanting gardens and a peaceful setting, guests will love this little slice of paradise in Southeast Ohio. The lovely property owners live on-site in a separate house and happily provide local history lessons, recommend local attractions and spoil guests with delicious homemade breakfast scones.

We truly enjoyed our overnight stay at the cottage, loved the peaceful location and chatting with the hospitable owners. Be sure to say hello to Zippy, the friendly orange cat who is the self-proclaimed official welcoming committee 😉 !

Where to Eat Along Ohio’s Winding Road

Triple Nickel Diner






Address: 1060 High Street, Chesterhill, Ohio 43728


Black Diamond Tavern

Address: 106 Main Street, Shawnee, Ohio 43782


Whether visiting for the day or long weekend, be sure to experience southeastern Ohio’s small towns, rich history and beautiful scenery. From historical tours, thrilling outdoor adventures to delicious dining options, there’s plenty of fun things to do along Ohio’s Winding Road!


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