With everyone buckled in, they drove to the Upper West Side to pick up four more dogs. Among those waiting was Elena Atkin, 59, a homemaker who works with various charities. She and her husband, Doug, a venture capitalist, adopted Emy, a Labrador mix, from a rescue organization in Sag Harbor, N.Y., but they didn’t want her sitting around the apartment all day.

So eight years ago, they signed Emy up for three hikes a week with My Dog Hikes. (She recently scaled back to once a week. On her off days, Emy goes running with a professional dog runner along the East River promenade.)

One of the program’s perks is an annual “pawrent teacher conference,” where owners and their dogs meet at a bar to mingle and talk about each dog’s behavior. It had taken place the previous night at Black Door, a dog-friendly bar in Chelsea.

“I got to meet Emy’s playmates,” Ms. Atkin said. “Emy has her own life outside of the home. Who knew?”

Once the dogs are comfortably situated, the team drives about 45 minutes to South Mountain Reservation in West Orange, N.J., a pristine 2,100-acre nature preserve with rigorous trails marked by a collection of miniature fairy houses. In the gravel parking lot, the dogs disembark one by one, so Ms. Klein and Ms. Godwin can sort them into groups and escort them onto the trail. Or rather, so the dogs can escort them.