Things to Do in Peekskill

Colossal train engines once pulled hefty freight along the O&W Railway's main line. Today, where the rails lines formerly cut through glistening tree canopies, a 2-mile unpaved trail splices through six rural hamlets, just 90 miles from New York City. It's along this rails-to-trails path that Woodridge Segway Tours whisks its adventurers through beautiful mountain views, clean country air, and the sounds of fresh water trickling. With safety helmets securely atop their heads, tour takers steer the two-wheeled segway transporters with intuitive gestures: leaning forward to go ahead, leaning backward to reverse, and pulling on their ears to make the segways sing.

After his daytime gig as a financial planner in Manhattan, Eli Newsom returns to his theatrical roots as artistic director of Bridgeport Theatre Company, a nonprofit founded by a band of Connecticut-based artists in 2010. Eli harnesses more than 15 years of performing and teaching expertise into each season's productions, which range from acclaimed dramatic fare to beloved musicals. The company’s ace staffers strive to bring each script to life with local actors and designers, and the BTC New Works program annually highlights the work of local playwrights, actors, and directors. In addition to its local cast and crew, each production depends on the aid of 25–50 volunteers, who lend a hand with countless tasks such as set construction, ushering, and haunting the theater dressed in a phantom costume.

In 2012, the Bluefish became the first team in Atlantic League history to reach 1,000 victories. It was a huge milestone for a franchise that today, stands as one of only two remaining charter teams throughout the entire league. The 'Fish initially brought baseball back to Park City in 1998, and advanced to the league championship series in a losing effort. A year later, though, they returned with their first league title after defeating the Somerset Patriots.

The team's early success established a winning tradition–in fact, the Bluefish didn't suffer their first losing season until their eighth year of existence. Winning hasn't been the only tradition in Bridgeport, however. The Bluefish battle the Long Island Ducks every season for the Ferry Cup, trying to establish regional supremacy on the baseball diamond instead of by firing a barrage of used baseballs across the Long Island Sound.

Situated at the foot of the Ellenville Mountain site, Mountain Wings has readied students for safe, engine-free flying since 1981. A staff of USHPA-certified instructors shares much of its knowledge on the facility's two training hills—a grassy, gently sloped concave for beginners, and a 180-foot hill used by intermediate gliders and a handful of pretty insane paper-airplane competitors. Sprinting, stumbling, and hovering across those hills, groups practice with Condors—slow-flying, easy-to-handle training gliders that work in zero-wind zones. Upon ascending to greater heights and skill levels, students can also snag their own equipment at Mountain Wings' full-service aero-sports shop.

Lifelong paintballers Glen Kapostas and Eric Schreiber founded Yankee Paintball with the aim of introducing new people to their favorite sport on a safe and fair playing field. Their 50 acres of paint-strewn battlegrounds include five different fields, each with a distinct layout and environment. Inflatable obstacles are scattered throughout the Airball Field, the layout of which changes every few weeks to enhance replay value. The 10-acre Castle Field—the largest of the bunch—spans the length of a small hill. Its battlegrounds light up with multi-colored crossfire during team games in which players crouch in bunkers, take shelter behind trees, and hide in the crowded nests of woodland critters.

The staff of Pocono Segway Tours leads groups of up to 10 sightseers on segway-propelled escapades through the scenic Pocono Mountains. A battery-powered personal transporter, the segway allows recreationalists of all shapes and sizes to navigate the gyroscopic machine along wooded paths and roadways while taking in the area's picturesque vistas during guided, multimile excursions. With two locations, the company gives tours in mountainous Split Rock; in Shawnee Inn, which presents views of the Delaware Water Gap.