1. Camino Schmidt (Puerto de Navacerrada → Cercedilla, 11 km) — the sierra’s signature traverse: yellow dots through high pines, miradores over the Fuenfría valley, and a train station at both ends. Bus 691 up, C-8 Cercanías home.
2. Calzada Romana de la Fuenfría (Cercedilla, loops of 2–4 h) — walk an actual Roman road: worn slabs climbing to the pass the legions used, signed loops from the valley information point, and the best effort-to-view balcony path in the range.
3. Peñalara (from Cotos, 2,428 m, ~700 m ascent) — the roof of the region: a steady signed climb from the C-9 mountain rail terminus, no scrambling in summer, glacial cirque views from the top. Real mountaineering in snow — know the season.
4. Laguna Grande de Peñalara circuit (from Cotos, easy) — the family version of number 3: a gentle signed hour and a half to a glacial lake under the cirque walls. The best reward-per-step in the Guadarrama.
5. Siete Picos ridge (from Navacerrada or Cercedilla) — the seven granite “peaks” that give Madrid its skyline: a proper ridge day with hands-in-pockets scrambling and both rail lines as exits.
6. El Yelmo from Manzanares el Real (La Pedriza) — the great granite helmet above the boulder chaos: a demanding signed walk to its base, griffon vultures overhead, castle views on the descent. Bus 724 from Plaza de Castilla.
7. Cascadas del Purgatorio (Rascafría) — a shaded valley walk to twin waterfalls in the Lozoya pines, starting near El Paular monastery. Best in May snowmelt.
8. Silla de Felipe II & Abantos (San Lorenzo de El Escorial) — the king’s stone seat and the forested peak above his monastery: 8 km gentle or a summit morning, then the town’s terrazas. Cercanías or Moncloa bus.
9. Senda del Genaro (El Atazar / Patones) — the reservoir-shore GR through black-slate villages in Madrid’s emptiest corner; do the Patones de Arriba stage and stay for dinner in the slate lanes.
10. Cuerda Larga (Navacerrada → Morcuera, 16 km, expert) — the range’s spine: five hours above 2,000 m, all sky. For fit walkers with an early bus and a taxi plan at the far end.
The Guadarrama is Spain’s best-connected sierra: the C-8 rail to Cercedilla, the weekend C-9 mountain line to Navacerrada pass and Cotos, bus 691 from Moncloa and bus 724 to La Pedriza cover eight of the ten walks. Weekend morning services fill — be at the station early.
Season notes: May–June and September–October are prime; summer works with a dawn start and pool finish (Las Berceas); winter turns everything above 1,800 m into mountaineering. Sleeping in Cercedilla or Navacerrada the night before buys you the empty first hours — hotels from around €45.
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