East Rock and Hamden Hills
If you’ve got a couple hours and want to find some cool riding, I recommend going up East Rock then hitting the Ridge/New Road/QU/Mt. Carmel area and back. Challenging, fast, not too trafficky, and scenic. If you’re in the Yale area (Bowl or Downtown?) there are easy routes to get there from wherever you’ve parked. The rail trail is definitely cool, but if you’re starting from the southernmost trailhead (currently easily accessible around Trumbull St/Hillhouse Ave. it’s very easy to get to, although it’s chopped up by many cross streets in the first couple miles.