Parking
Madison Run Boundary on Route 663 near Route 708; roadside parking for about eight cars by the junction. Keep clear of gates.

Shenandoah National Park, VA
A demanding four-day loop links ridges, waterfalls, and Big Run.
Overview
This is a demanding four-day backcountry loop from Madison Run Boundary. It crosses Furnace and Trayfoot mountains, follows Paine Run to Skyline Drive and the Appalachian Trail, then descends Jones Run and Doyles River before turning through Big Run Portal, Rockytop and Austin Mountain. The itinerary classifies it as experienced or advanced. It lists 36.1 miles for the base trip; the connected trail line measures about 33.3 miles, so expect some distance variation. The route stored here leaves out the optional 8.7-mile Brown Mountain circuit and the one-mile round-trip Furnace summit spur.
Parkwolf’s verdictIs this the hike for you?Map & elevation
Plan your hike

The highest, rockiest slopes around here are a summer buffet for grizzly bears.
Shenandoah Tour Guide
Parkwolf is a GPS audio tour guide for Shenandoah National Park. As you drive, it chimes in with what’s ahead: hidden gems, upcoming stops, history, geology, and wildlife, right through your car’s speakers.
See the Shenandoah audio tourMore stories near here in the app
Trail guide
Start at the Madison Run boundary gate and take 0.1 mile of fire road to Furnace Mountain Trail. Roughly 1.6 miles along Furnace, a side trail to the summit adds one mile round trip and reaches the viewpoint described in the itinerary; it is an extra, not part of the stored line. The base route continues 3.4 miles on Furnace Mountain Trail and 4 miles along Trayfoot Mountain Trail before joining Paine Run. Find an established legal backcountry campsite along Paine Run; the first night’s distance varies with the site you choose.
On the second day, continue up Paine Run to Skyline Drive, then cross to the Appalachian Trail. Follow the AT north for 2.6 miles before descending Jones Run. A short side trail near mile 1.7 leads to the falls viewpoint; the main route continues to the Doyles River junction at about 2.5 miles. From there, follow Doyles River Trail for 2.2 miles, cross Skyline Drive, and reach Big Run Overlook. The trip description calls out three waterfalls along the route, with Jones Run’s falls viewpoint as a memorable stop.
Descend Big Run Loop Trail for 2.2 miles to Big Run Portal, then follow the stream valley to a legal campsite. Camp location changes the mileage. Multiple crossings on Big Run Portal can reach knee or waist depth when water is high, especially in spring or after heavy rain. The last day continues down Portal before climbing Rockytop for 5.3 miles and Austin Mountain for 3.2 miles, then follows Madison Run Fire Road 0.7 mile back to the same boundary. That return day is long; allow room in your schedule for the climbs and crossings.
Overnight camping requires a backcountry permit, and campers must use legal sites. The itinerary recommends an early start on day one and lays out four days of substantial hiking. Plan campsite locations before setting out because they change the day-by-day distance. Dogs are allowed on this route but must stay on a physical leash no longer than six feet; pack out pet waste.
Start and finish at Madison Run Boundary on the west side of the park at Route 663, near Route 708. Roadside parking is listed for about eight cars by the junction; keep clear of gates. This is a small road-edge access, not a large day-use lot. The first mapped trail point is a short walk from the boundary access.
Wildlife
325 sightingsBlack BearMost seen around 6 AMSighting map
21 sightingsBald EagleMost seen around 10 AMSighting map
1,036 sightingsWhite-tailed DeerMost seen around 7 PMSighting map
167 sightingsWild TurkeyMost seen around 7 AMSighting map
93 sightingsTimber RattlesnakeMost seen around 6 PMSighting map
24 sightingsCoyoteMost seen around 6 AMSighting mapSighting maps show where each species has been reported across Shenandoah. Wildlife moves, so no sighting is guaranteed.
Keep exploring
ChallengingFurnace Mountain, Jones Run, and Austin Mountain Loop17.6 mi · 15 hr · At the trailheadThree waterfalls and a rugged two-day loop over southern ridges.
ChallengingPaine Run, Doyles River, and Austin Mountain Loop25.8 mi · 18 hr · At the trailheadThree waterfalls on a three-day, 25.8-mile backcountry loop.
ChallengingFurnace Mountain - Austin Mountain Loop12.8 mi · 8 hr · 0.1 mi awayA hard mountain loop with a boulder summit and rough talus.
ChallengingFurnace Mountain Trail4.4 mi · 3.5 hr · 0.1 mi awayA rocky climb to a summit outcrop with views on both sides.
ChallengingFurnace Mountain, Jones Run & Big Run Loop25.4 mi · 22 hr · 0.1 mi awayThree waterfalls, a wild valley and a two-night backcountry loop.
ModerateJones Run Falls Hike3.2 mi · 2.5 hr · 3.1 mi awayA wooded descent to a 42-foot cascade, then an uphill return.
EasyBlackrock Summit Loop1 mi · 1 hr · 3.2 mi awayA one-mile circuit to a boulder slope and Shenandoah views.
ModerateLewis Peak via Rockytop Trail9.1 mi · 5 hr · 3.5 mi awayA long, rocky ridge hike earns an open summit ledge.
Sight · 0.9 mi awayFurnace MountainAn open rock ledge earns the climb with sweeping valley views.
Sight · 3.1 mi awayBlackrock SummitA short loop to a boulder summit and a wide Shenandoah view.
Scenic pullout · 3.1 mi awayDundo OverlookA quick pullout for Massanutten and the valley beyond.
Picnic area · 3.3 mi awayDundo Picnic GroundsA shady picnic stop with a small Civilian Conservation Corps story.
Scenic pullout · 3.9 mi awayTrayfoot Mountain OverlookA quick Skyline Drive pullout for layered mountain views.
Sight · 4.1 mi awayJones Run FallsA 42-foot cascade; save energy for the uphill return.
Scenic pullout · 4.3 mi awayDoyles River OverlookA south-facing cove view with a history worth pausing for.
Scenic pullout · 4.5 mi awayHorsehead OverlookA quick Skyline Drive view with a story in the rocks.Parkwolf’s Shenandoah ranking