Urban Hikes & Trails in Connecticut Last Updated: September 2023

Meet our #CTcreator Chandler Anderson! CTvisit.com is proud to partner with some of the region's most popular content creators for ideas, insights, and inspiration from the people who are lucky enough to call Connecticut home, like photographer Chandler Anderson, who wrote this article. Article has been updated by the Connecticut Office of Tourism.

Harbor Point - Stamford, CT

City of Stamford, Stamford

This location is a whole vibe. Harbor Point is a thriving waterfront redevelopment, has over 15 restaurants, 10 apartment complexes, 20 acres of parks, and easy access to the Metro-North train station. During my visit here, I made a point to take a walk along the Harbor Point 2-mile boardwalk. It wasn’t strenuous at all as it is flat. The highlight of the walk was enjoying the waterfront view—it feels amazing to have that escape all while being in the city.

Seaside Park - Bridgeport, CT

Seaside Park, Bridgeport

This 325-acre waterside park provides picturesque views of the Long Island sound. Seaside has a little something for the whole family to enjoy. There’s a playground, ball fields, beach, fishing access, hiking trails, and many historical landmarks to view. One of my favorite things to do here is walk the seaside beach path; you can walk over 4 miles while on it. This path can be enjoyed by walkers, joggers, bike riders, and has accessibility for strollers and wheelchairs.

West Ridge Rock State Park - New Haven, CT

City of New Haven, New Haven

West Ridge Rock is a massive 1,700-acre park with over 20 miles of hiking. The park is so long that it borders over 3 towns. One of the most popular features of this park is the 627-foot West Rock that provides panoramic views of New Haven and Long Island sound. There are multiple ways to get to the vista point. You can drive up or hike the blue, green or red trails. One of the most popular trails to the vista point starts at the West Rock playground. From the playground to the vista point is about .8-mile moderate challenging hike. 

New London Waterfront Park

Located along the Thames River in Downtown New London, the waterfront park offers picturesque views of the harbor; it gives easy access to several restaurants and shops, and the ability to access the New London train station. The waterfront park is home to the annual summer Sailfest. During the festival, there are tons of vendors, entertainment, and of course a huge firework display. Although there’s no exact trail at the park, I personally think it’s the best part. No trail means you have opportunity to pave your own path and make your own unique adventure out of it.