Chinchon, 55 minutes from Madrid by bus, is the 17th-century arcade-plaza Castilian town with cordero asado at Meson Cuevas del Vino (a 1648 wine-cellar dining room) and the Anis de Chinchon liqueur tradition.
Tip: Bus 8 euros each way. Cordero asado lunch on the Plaza Mayor terraces 32 to 38 euros. Try Anis Chinchon Especial at the bar.
San Lorenzo de El Escorial, 1 hour from Madrid by Cercanias, is the royal-monastery town with Castilian-roast canon at Charoles (Michelin Bib Gourmand since 2010) and the high-altitude wine tradition from the Sierra.
Tip: Cercanias 10 euros return. Charoles books up two weeks ahead for weekend lunch; carte 45 to 60 euros per head.
Valdemoro, 30 minutes from Madrid by Cercanias, is the suburb-and-Manchego frontier where Chiron (1 Michelin Star since 2014) cooks the canonical Castilian cocido madrileno in clay pots and the regional roast tradition.
Tip: Cercanias 7 euros return. Chiron tasting menu 65 to 95 euros; book three weeks ahead for weekend lunch.
Alcala de Henares, 45 minutes from Madrid by Cercanias, is the UNESCO heritage university city where Cervantes was born, home to the Costrada de Alcala almond cake at Casa Salinas and the Mostrador university dining tradition.
Tip: Cercanias 8 euros return. Costrada de Alcala 14 euros per cake; whole costrada to take back to Madrid. Lunch on Calle Mayor at 14:30.
Segovia, 30 minutes from Madrid by AVE, is the Castilian wood-oven capital, with Meson de Candido at the foot of the Roman aqueduct serving cochinillo asado since 1860 and Jose Maria running parallel on Calle Cronista Lecea.
Tip: Book Candido or Jose Maria three days ahead for cochinillo. AVE 14 euros each way; 30 minutes. Cochinillo lunch 38 to 45 euros.
Toledo, 33 minutes from Madrid by AVE, is the marzipan capital of Spain with Santo Tome and Casa Telesforo making the canonical almond-and-honey treats since the 14th century, plus venison and partridge stews at the old Manchego tabernas.
Tip: AVE 14 euros each way. Buy marzipan whole boxes from Santo Tome (24 euros per kilo). Lunch at Adolfo for the venison.
Aranjuez, 45 minutes from Madrid on the Cercanias C-3 train, is the royal-garden town with the spring strawberry tradition (fresas con nata at Casa Pablo) and the white asparagus from the Tajo riverside.
Tip: Cercanias 8 euros return. Strawberries peak in April and May. Casa Pablo for the strawberry-and-cream order at 13:30.