The Perfect Weekend in Fentress County, Tennessee

Start here. The Twin Arches are the largest twin sandstone arches in the entire eastern United States — the North Arch stands 62 feet tall and the South Arch is 70 feet tall with a 135-foot span — and they will stop you in your tracks. The loop is an easy 5 miles with manageable terrain, perfect for warming up without destroying your legs before the rest of the day. You can walk across the tops of both arches. There is simply nothing like this anywhere else in Tennessee.

If you’re a serious hiker: Drive to Honey Creek Loop (45 min from Twin Arches via Hwy 154 S to Burnt Mill Bridge Rd). This is widely considered the best day hike in all of Big South Fork — 5.5 miles of waterfalls, caves, slot canyons, boulder scrambles, and multiple creek crossings. You will get wet. Bring extra socks. Allow 4+ hours. Challenging and completely spectacular.

If you have kids or tired legs: Drive to Bandy Creek Campground (30 min from Twin Arches). The swimming pool is open Memorial Day through Labor Day — clean, cold, surrounded by forest. Have lunch from Jamestown and recharge at the pool. Pick up a trail map at the visitor center for after.

Drive scenic Hwy 154 south to Pickett State Park — one of Tennessee’s least-known gems, sitting right against Big South Fork. The Hazard Cave trail is a compact 3.5-mile loop with a massive walk-in rock shelter and natural bridge — perfect for an afternoon when you’ve already done a big morning hike. Arch Lake is a hand-built CCC lake from 1934 surrounded by ancient forest — bring a blanket and just sit for a while. If it’s a clear night, come back after dark — Pickett is Tennessee’s only certified International Dark Sky Park.

Highland Manor Winery sits right in Jamestown and is one of those places that surprises everyone who finds it — Tennessee’s oldest licensed winery, producing award-winning wines for over four decades. Free tastings and guided tours in a historic manor setting. After the winery, dinner in Jamestown: Garcia’s Mexican or El Azul for a satisfying sit-down meal after a day on the trail. If it’s a Saturday, Sawbriar Brewing has live music and wood-fired pizza — easily the best evening option in the county.

Drive north on Hwy 127 to Pall Mall — the tiny community on the Wolf River where Alvin York was born in 1887, became the most decorated American soldier of World War I, turned down every offer of fame and fortune, and came home to build a school. His gristmill, the York family homestead, and his grave are all here — quiet and unhurried, the way small historic sites should be. The Wolf River on a Sunday morning in Pall Mall might be the most peaceful place in Tennessee.

Dale Hollow Lake is 27,700 acres of crystal-clear water holding the still-standing world record smallmouth bass (11 lbs 15 oz, 1955). Drive down to Sunset Marina off Hwy 111 in Monroe — one of the most accessible marinas on the lake, right off the highway. If you have fishing gear, the smallmouth here are world-class. If not, swimming and simply being on the water is reason enough. Lunch at the marina bait shop or pack your own. The lake looks like something out of the Canadian Shield — visibility to 20 feet, blue-green water, quiet coves.

The drive back through Jamestown is worth slowing down for. Stop at West End Cafe if they’re still open (closes at 3pm) for coffee and homemade pie. Browse downtown Jamestown — small town, genuinely charming, not manufactured. If you want one more outdoor stop, the drive down Hwy 154 through the plateau forest toward the Big South Fork entrance is one of the most beautiful 15-mile stretches of road in Tennessee — even without stopping, it’s worth the detour.