Best trails in New Haven, Connecticut

Rugged cliff-walk with spectacular views of multiple lakes and busy highways below. Mostly a level walk along a ridgeline going south to north. You get there by going through the West Rock Ridge State Park entrance off Wintergreen Avenue in Hamden. Follow the signs up the hill to the South Overlook about 1.2 miles. There is a large parking lot at the top of the overlook with incredible views of New Haven and Long Island Sound on a clear day. The trail is clearly marked with blue blazes. The northern terminus trailhead is located right behind the South Overlook shelter. The trail is mostly easy going but there is a two (+) mile stretch, right in the middle of this seven mile trail, that includes a lot of rock hopping ankle-breaker rocks that tends to slow you down. The rest of the trail is a really enjoyable hike with plenty of shade. At the northern terminus of trail it joins the Quinnipiac Trail (blue blazed) and the clearly marked Sanford Feeder (blue-red blazed, 0.6 mile) which connects the Regicide Trail with Brooks Road in Bethany. There is road-side parking on Brooks Road at the end of the Sanford Feeder.Show more

The Westville Feeder is just a quick out & back that you can easily fit into a morning or afternoon. As an add-on to this feeder trail, you can continue onto the Regicides Trail which leads you up a short ways to Judges Cave where Edward Whalley and William Goffe hid out in the 1660s trying to evade retribution from Charles II whose father (King Charles I) they had sentenced to death in the 1640s.Show more