As you wind your way through the leafy woods and unmarked dirt trails up to East Rock, gaining elevation, the city of New Haven will begin to flit in the distance. Beyond it, the Long Island Sound unfolds, stretching a deep blue into the distance. Pause, sit, and take in the panorama. It’s an intimate way to share a moment with the city.Once you get to the top of East Rock—whether by foot, bike, or car—you can look up at the Soldiers and Sailors Monument, one of New Haven’s iconic landmarks, visible from all across the city. The monument, which stands 112 feet high and dates back to 1887, honors citizens of New Haven who lost their lives in the Revolutionary War, the War of 1812, the Mexican War, and the Civil War. At night, it projects a set of bright lights into the sky, sometimes in a whole array of colors, that anyone can see if they stretch their head out the window.

If you live in New Haven, you’ve most likely been to the top of East Rock. The long trap rock ridge is on the north side of the city, its cliffs rising dramatically above the quaint neighborhoods and playgrounds below. The lookout is part of the Metacomet Ridge, which extends from the Long Island Sound all the way north to the Vermont border. The most dramatic and rewarding way to experience East Rock is via the slightly precarious Giant Steps Trail. You can access the trail from East Rock’s eastern side: It’s a jagged stone staircase, equipped with a metal handrail, that takes you the last 285 feet to the top. (In 2011, a Yale University student was rescued by firefighters after trying to free climb part of the cliff face, which needless to say is not the recommended route to the summit.)In the winter, people can snowshoe and cross-country ski to the site through East Rock Park. In the summer, families often drive up and picnic at the top. At night, from the summit of East Rock, beneath the monument’s strobes, you can sit and watch the city twinkle peacefully.