Flanked by cypress and palm trees, the graceful, 1923 Redlands Bowl amphitheatre—a treasured structure in this surprisingly elegant city—stands out as one of the most appealing venues in the region. With its arched, red-tiled bandstand (known locally as “The Prosellis”), the site hosts the country’s oldest continuous free concert series, offered every summer since Redlands Bowl first opened. You’ll hear everything from classical music to foot-thumping bluegrass bands—all free, every Tuesday and Thursday night at 8 p.m. in June and August (be sure to check with their official site for schedule details). Bring a blanket and pack a picnic to enjoy on the bowl’s sloping lawns, located on either side of the stage (there are benches too, if you’re not feeling quite so kickback.)
It’s recommended that you show up early for any performances, as seats can disappear fast, especially for the summer free concert series. For a pre-concert dinner , there are plenty of nearby options. Bricks and Birch serves wood-fired pizzas and pastries, while Redlands Oyster Cult make you feel like you’re on the California coast with its top-notch seafood menu. For a truly decadent meal, head to Rok n Fondue, a steak, fondue and craft cocktail and beer joint that also has a nice selection of wines. Afterward, make the short stroll over to the Bowl—summer evenings don’t get much more California-classy than this.
While in the area, be sure to pencil in time to check out some of Redlands’ other attractions. The Lincoln Memorial Shrine, which is adjacent to the Redlands Bowl, has extensive grounds and artifacts and exhibits devoted to both the 35th president and the Civil War. Another attraction that makes for a leisurely afternoon spent outdoors is the Kimberly Crest House & Gardens, two miles south of downtown. Visitors can take a tour of the 1897 estate’s museum and lush, Italian Renaissance–style gardens (advance reservations required).