Kyustendil – Osogovo Chalet / 1st option – via the Hissarluka Park
Set from the town's market as a starting point. Head southwards along the cemented stairway, which leads to the Hissarluka Park. The waymarks are red and available from this point. The trail leads onto the road, which links the town of Kyustendil with Osogovo chalet through the village of Bogoslov. After approximately 200 m turn left onto a cobbled alley (the second along the road). The trail enters a coniferous forest and goes past a drinking water tank, after which you should turn left. The alley rises along a stony slope, passes by the zoo and after approximately one hour reaches the Cheshmeto restaurant.

Hikers should follow closely the waymarks as from this point several other paths and alleys begin. The route continues to the right of the restaurant along a broad alley. After approximately 15 – 20 minutes it crosses the asphalt road and continues along the path on the left. The route passes through an oak forest, and then enters once again a coniferous one. After approximately 600 m the route goes once again onto the asphalt road, which takes you to the village of Bogoslov. The distance up to this point is a little over one hour. The road leads to the Osogovo chalet.

Kyustendil – Osogovo Chalet / 2nd option
The starting point is the building of the Regional Directorate of the Ministry of the Interior. Head southwest, along the street, going by the left side of the stadium, then continue along an asphalt road, leading to the Hissarluka Park. Approximately 50 – 60 m from the upper end of the net of the stadium, on the right-hand side of the road, a path, waymarked in red, veers and leads through a coniferous forest to asphalt road, linking Kyustendil and the village of Bogoslov. The two trails (this one and the one from option 1) meet, and the route continues along the road to the village. From the upper end of the village, head southwest along a marked stony path. It reaches the drinking water tank, where the path forks. The left branch crosses the asphalt road and the trail goes slightly uphill. After approximately 15 minutes the route goes onto the road again.

The trail crosses the road and works its way up the path, which runs for approximately 1500 m parallel to the asphalt road (on its right side), followed by a steep climb through a beech forest. The path passes under Grob peak (1320 m) and leads to Gorna Popova Livada area. It meets the marked trail, coming from Dolna Popova Livada; the two converge and lead to Osogovo chalet.

If you take the right branch of the path from the water tank, you will reach a steep switchback, which after approximately 150 m will lead you to the asphalt road at a sharp left turn. At the turn, the trail veers to the left onto a dirt road, on which you should continue. It crosses the Grob peak from the north through a beech forest and goes onto Dolna Popova Livada area.

Osogovo Chalet – the Prevala Area (Beg Bunar Well) – Ruen Peak (2251 m)
The most popular and the most preferred route used by hikers to Ruen peak. There are red waymarks, available on stones and trees as well as on metal stakes, which is actually the winter marking. The one-way distance takes approximately 4 hours to cover with an average firm tread. Head south from the chalet along the asphalt road and after some 200 m turn right onto a broad dirt road, which after approximately 15 minutes reaches the Gramadite area – a gently sloping grassy plateau, strewn with granite rock fragments. The route continues westwards though pastures, also strewn with granite pieces, crosses the Kulin Kamuk peak from the south and passes below the springs of the Mlachka river. The trail goes slightly uphill and crosses from southeast and east of the Choveka peak, then goes onto the Prevala area, where the Beg Bunar fountain is located. The walking distance up to this point is one hour and 30 minutes. In 2007 Osogovo Tourist Association transformed the former border fort into a cosy shelter.

The route continues towards the Tsuren Kamuk peak, then immediately before it crosses the ridge and goes on its south side to divide before the Shipka peak. The right branch goes down to the valley of the Bistritsa river, while the left leads to Shipka shelter (another former border fort). The walking distance from the Prevala area to this point is approximately 1 hour and 15 minutes. Some 30 – 40 m south from the shelter there is a small fountain with drinking water. The route to the peak forks right off the dirt road and goes gently upward along the southwest slope of the Shipka peak. Go to the top of the ridge, continue past the Gorna Solunka ridge, which appear on your left and then past the Mali Ruen peak. With Mali Ruen right from the path, the trail reaches the grassy slopes of the Ruen Peak. The distance from Shipka shelter to the peak is about 40 minutes. Just below the peak is Ruen shelter, built in 2006 by the Osogovo Tourist Association. The shelter has two premises, equipped with benches and tables.

Ruen peak is the fifth highest peak in Bulgaria after Musala, Vihren, Botev, and Cherni Vruh. It is the highest border point of the European Union.

Osogovo Chalet – Tsurnotrav peak – the village of Vratsa
The waymarking is in blue. It starts from Osogovo chalet.

Ruen Peak – the village of Gyueshevo
The trail from the top goes north in an immediate proximity to the Bulgaria- Macedonia border line. In both directions permission from the border police is required. The distance on the way down is 3 – 4 hours, while the way up, because of the steep terrain, takes approximately 4 and a half – 5 and a half hours. The trail is waymarked in red. The way downhill begins through grassy areas and swerves sharply towards the foot of the Kamenets peak (1994 m). After a slight ascent, it crosses the peak from the right. Then the trail forks and its right branch leads to Kulata peak.

The route to Gyueshevo continues northwest, once again along controlled access border zone. It goes past the remains of a former Macedonian border fort and just above the village of Gyueshevo makes a right turn. Leave the path here and continue straight downhill (there is no marking) to the forest belt, in front of which there is a small well. Enter the forest and continue along one of the numerous dirt roads or go at random to the Skopje- Kyustendil road. Left from the road is the turn-off to Gyueshevo. A railway line links the village with the town Kyustendil, and on holidays, the train continues to Sofia.

Osogovo Chalet - Sokolov Kamik peak – the village of Vratsa
Start from Osogovo chalet along the path with blue waymarks and follow it to the ruins of an abandoned sheep-shed. Leave the path and continue to the right down a steep meadow, interspersed with juniper and small rocks. After 150 – 200 m there is a rock with a triangular point (1684 m above sea level), named Sokolov Kamik. In the western end of the meadow the walls of the Vratechki Govedarnik shelter are visible.

In the past the Sokolov Kamik peak was the training location of the Alpine Club in Kyustendil. After passing the peak, go down to the lower end of the meadow, from where the trail along the stony Murata hill starts. It is not waymarked, is overgrown and difficult to navigate. The trail crosses the small Elinska river and goes down through the Rekalska settlement to the village of Vratsa. The distance to the village in this direction is 3 hours and 30 minutes, and the way back takes 4 hours and 30 minutes.

Osogovo chalet - the Raskola area – the Eshekchiyska Ornitsa area – the Choveka peak – the Prevala area – Karakashka settlement – the Tri Buki tourist complex – Osogovo chalet
The route is waymarked in green. Start along the asphalt road to Kyustendil in northeast direction. After approximately 700 m there is a junction of black forest paths. Turn left (northwest) and go onto a big meadow, known as Eshekchiyska Ornitsa. Continue westwards along a dirt road, leading though a beech forest, and cross the Kyunik peak (1923 m) from the north to reach the small flat peak of Platno. The Osogovo chalet – the village of Vratsa trail and the winter route to Ruen peak also pass though here. Follow the waymarks to reach the Choveka peak.

Go down southwest to the Prevala area. The length of the route up to here is 2 h. and 30 min. Along this route hikers can also go down to the Tsurna Reka reserve. From the Prevala area in southwest direction a dirt road crosses the Gorna Chuka (1802 m) and the Dolna Chuka (1751 m) peaks and descents to the ridge to the Karakashka settlement, making a sharp turn left to the east. In winter the Prevala area – the ridge to the Karakashka settlement section should be covered through the ridge since the region is highly avalanche-prone. After the Karakashka settlement the route goes onto the road, leading to the building of Osogovo State Game - Breeding Station. From there, the trail goes onto an asphalt road, which passed the Tri Buki tourist complex and leads to Osogovo chalet.

Osogovo Chalet - Golyam Predel area - Brezovo hill – the village of Slokoshtitsa
The route follows mainly the ridge of the mountain and offers breathtaking views. Its length is 8 – 9 hours, and the waymarking is in yellow. With Osogovo chalet as a starting point, follow the asphalt road in the direction of the Tri Buki tourist complex, go past the complex and continue along the ridge trail to the holiday house (a prophylactics centre) of the State Auto Transport Enterprise (1527 m). Continue uphill through the meadow, opposite the prophylactics centre, enter the beech forest and cross the Chukata peak (1628м) from the left. The trail then leads to a meadow, from which the Cherni Vruh peak (1695 m) can be seen. A dirt road crosses the peak from the left and the trail descends to saddle in front of the Yurushki Grobishta peak (1551m). A gentle incline leads down to Virovete cold spring. From here follow the marked ridge trail to the Golyam Predel area (approximately 1 hour). In the Golyam Predel area runs the Kyustendil – the village of Sazhdenik macadam road.

Here, Brezovo hill, a landmark of the mountain, begins. Along the main ridge of the hill, from south to north, rise the following higher peaks: Golyama Chuka (1454 m), Kostina Chuka (1474 m), Belotok (1524 m), Taushanska Chuka (1297 m) and Sipelyo, lying above the village of Slokoshtitsa and covered with coniferous forests. The distance from the Golyam Predel area to the Belotok peak is one hour. Continue along the ridge. Above the village of Slokoshtitsa there is a coniferous forest through which you can go down to the village (Slokoshtitsa), located 2 km away from Kyustendil. The distance along the ridge from the Golyam Predel area to the village of Slokoshtitsa is 15 km. Just before the route enters the coniferous forest there is a broad cart track on the right. It is waymarked and leads to the Monastery of St Luka above the village of Granitsa. The distance from the turn-off is about 20 – 30 minutes. An asphalted road leads from the monastery to the village. The distance is 1 hour.