About this Itinerary
Beginning in the late 1700s, thousands of pioneers setting out for Kentucky and other points west, traveled the Wilderness Road in Virginia and went through the Cumberland Gap, earning the area the moniker ‘Gateway to the West.’ The route through ‘the gap’ was steep and narrow and could only be navigated on foot or horseback. In addition, there was the constant danger of robbers, but for many the risk was worth it in pursuit of a better life. Today, bike near this hallowed route, under considerably less stressful conditions, and immerse yourself in the dramatic history of this southwest corner of Virginia.
The Cumberland Gap is a natural passageway through the Cumberland Mountains where Virginia, Kentucky and Tennessee come together. Native Americans hunted along this route for centuries but it was not until Dr. Thomas Walker explored the area, and later Daniel Boone established the Wilderness Road, that settlers used this passageway. ‘The gap’ was also a strategic location during the Civil War and held at various times by both Confederate and Union soldiers, although no significant battles took place here.
Our route on the Wilderness Road Trail (WRT) takes you along a trail that follows part of the original Wilderness Road carved by Daniel Boone, and later became a corridor for the Louisville and Nashville Railroad. The WRT is an 8.5-mile crushed-stone trail that travels from near the Virginia/Tennessee border to the Wilderness Road State Park. On this itinerary we will bike from our recommended hotel in Cumberland Gap, Tennessee, through a section of Cumberland Gap National Park to Wilderness Road State Park for an 11.5 mile route (23 miles roundtrip). This route does include some inclines and potential rutted paths, therefore, a mountain bike is highly recommended.
The town of Cumberland Gap, Tennessee is nestled at the foothills of the Cumberland Mountains and is surrounded by Cumberland Gap National Historical Park. The location provides an ideal base for biking the WRT as well as for further exploration of the national park. Cumberland Gap was a postal town that was established in 1803 but not until 1907 did it become incorporated. The town has the only post office in the country that has been in three states (Tennessee, Kentucky, and Virginia), but in 1885 it was finally established as being in Tennessee, where it remains. Today this charming and historic town features a number of restaurants and shops and the 25,000 acre Cumberland Gap National Park is just steps away.
In Cumberland Gap, stay at the historical The Olde Mill Inn B&B. Built in the mid-18th-century, the property features seven rooms with private bathrooms and comfortable common spaces. A full hot breakfast is included in your stay, and the inn is close to shops and trails that will take you directly in to the national park. To reach the inn from the airport in Knoxville, take I-75 N to TN-63E and TN-32 to State Road 872 to Cumberland Gap. Turn left on Pennlyn Avenue in town.
Note that bicycle rentals are not available in Cumberland Gap or surrounding towns, so you will need to bring your own. If you are driving from Knoxville, that town is your best bet for a mountain bike rental. Tennessee Valley Bikes offers mountain or hybrid bike rentals for multiple days and is only about 20 minutes from the airport in Knoxville, in the direction you are heading.
During the ride you will be able to fill water bottles; however there are no opportunities to purchase food. There are outstanding opportunities to enjoy a scenic picnic lunch though, so before setting out, be sure to purchase everything needed for the day. At the Gap Creek Coffeehouse, located just a couple of blocks from the inn on Pinnacle Alley, you will find fresh homemade sandwiches, delicious snacks, and cold drinks to pack for a lovely picnic. Plan ahead as they do not open until 10 a.m. One block over on Brooklyn Street is the Cumberland Gap Market, a small grocery store, which can also provide the fixings for a nice meal on the go.
After a hearty breakfast, with your water bottles full and lunch packed, bike from The Old Mill Inn three miles to the start of the Wilderness Road Trail. Head east on Pennlyn Avenue and turn left on to N. Cumberland Drive. Look for signs for the Boone Trail (on the left) and take a sharp right to enter the trail. Follow this downhill route (do not be confused by the Wilderness Trail that heads uphill from the Daniel Boone Visitor Center and is not the bike trail) and connect on to the Colson Trail when you reach the Wilderness Road Campground area (you will pass over the National Park Road). Continue following the trail through the campground where it eventually connects with the Wilderness Road Trail. For those who prefer to drive to the trailhead: head to N. Cumberland Drive and follow signs for State Road 872, turn left on US-58E and look for Wilderness Road Campground.
The WRT parallels US-58 for its entire length, although only during the first two miles will the road be visible. Along the remaining section of the trail, see the Cumberland Mountains in the distance as you travel through farmland before reaching the trail’s end at the Wilderness Road State Park. As noted, the WRT is a crushed stone and gravel trail. Some sections are rutted, and especially after rainfall, the trail can be a bit challenging. Also be aware that this is a popular horseback riding route, so be careful when approaching so as not to spook the animals (or their riders). You should expect a peaceful, tranquil ride and not a lot of crowds, especially once you are away from trailheads.
The Wilderness Road State Park is the eastern terminus of the WRT. This park offers picnic tables, restrooms, a visitor center, a museum and living history programs. Stop in to the visitor center to see the short film that gives background on the Wilderness Trail; visit the frontier museum to see artifacts and exhibits about the pioneers who traveled this dangerous route; and watch a historical interpretation of life in 1775 Virginia at Martin’s Station.
Upon your return to the western terminus of the WRT, and the Wilderness Road Campground, stop to enjoy some of the hiking trails in this area and use the opportunity to enjoy your picnic lunch if you have not yet eaten. The Greenleaf Trail departs from the northeast end of the campground and takes you on a leisurely route slightly less than a mile through old hardwood forests. See posted signs for options for longer hiking routes. Note that only designated trails in the park are open to bicycles. Do not bike on any trail until you know that it bike accessible.
Head back toward Cumberland Gap on the uphill route to the Daniel Boone Visitor Center. Wander through the outdoor pavilion to see the small exhibit featuring the sights and sounds that pioneers would have experienced coming through ‘the gap.’ At this visitor center, you can also purchase tickets for Gap Cave Tours. (If you are there in high season you should book these popular tours in advance; reservations are taken up to one month prior.) The tour is a two-hour ranger-led excursion into the magical underground world of the mountain’s cave system. Visitors will see stalagmites, flowstone cascades, and may catch a glimpse of a bat. The tour is considered to be moderately strenuous, covering 1.5 miles on four levels of the cave and including 183 steps.
Also departing from the Daniel Boone parking area, join a 4-hour ranger-led tour of the Hensley Settlement. Located on the top of Brush Mountain, the tour includes a shuttle ride to the settlement and a one mile walk through the property. On-site you will see historical buildings that remain from the 1904 settlement that was established by Sherman Hensley and that were occupied until 1951.
After a long day biking and exploring parts of the Cumberland Gap National Park, return to the comfort of The Old Mill Inn to relax on their creek-side deck or spend time wandering through the historical town’s many shops.
The dining scene in Cumberland Gap is somewhat limited and dinner options are relatively non-existent as several restaurants have closed in recent times. Check with your hosts about any new restaurants that may have recently opened. Otherwise, your best bet for dining is heading to nearby Harrogate or Middlesboro, Kentucky. In Harrogate, find Heavy’s BBQ, which may not look like much from the outside, but is the real deal in terms of authentic, quality BBQ. The restaurant features all the favorites from baby back ribs, pulled pork or chicken, and much more. Also in town find Angelo’s in the Gap which serves a variety of Italian specialties as well as pizza. In Middlesboro, try Shades Steakhouse. This restaurant features steaks, chicken and pork, and is open Thursdays through Saturdays. Also try Pelancho’s Mexican Grill, a regional chain serving fresh Mexican-inspired cuisine.
Biking the Wilderness Road Trail is only the tip of the iceberg in terms of exploring Cumberland Gap National Park. Stretching for 26 miles along Cumberland Mountain and containing 24,000 acres, the majority of the park is a second- and third-growth eastern hardwood and conifer mix forest. The woods are home to a diversity of species including white-tailed deer, black bear, rabbit, raccoon, and wild turkeys and there are more than 24 known entries to limestone caves. Stop by the main Visitor Center, located west of the town of Cumberland Gap on Route 25E, to pick up maps and helpful advice on the numerous hiking trails in the park, as well as other routes that are accessible by bicycle. Also learn about different events that may be taking place during your stay, tour the hands-on museum, and see films about the park and early pioneers. The center also sells crafts from artisans representing Appalachia and visitors can often observe demonstrations of quilting, woodworking, weaving, and pottery-making.
In the town of Cumberland Gap, visit the Little Congress Bicycle Museum, a fascinating collection of bicycles representing over 41-years of private collecting. This museum dedicated to the bicycle is a labor of love for the curator, Judge R.E. McClanahan II. Admission is free and the museum is located just steps from The Olde Mill Inn. Also see the Iron Furnace, located just up from the town center; this is the remains of an iron furnace where limestone and iron ore were heated by coal and converted to ‘pig iron’ before being shipped to factories. The furnace was in operation from about 1820 to 1880.