New York, New York
Play: While Central Park doesn't require leashes before 9 a.m., Tompkins Square Dog Run — the first and largest off-leash dog park in New York City — is still the best place to let your pooch run wild and free at any given time of the day. Swing by the park's greenmarket on Sundays then sit (and throw the ball) from a picnic table at this picturesque East Village haven for hounds big and small. The city has over 55 NYC dog parks, but this one is reliably fun and full of playmates. Plus, it has dog bone-shaped pools.
Stay: To get the most bang for your bark, book a room (from $224, plus a $50 pet fee) at The Benjamin in Midtown Manhattan. The hotel's goodDOG program with BarkBox includes pet beds, a collapsible water bowl, toys, treats, a roll of plastic dog bags, and an in-room pet mini bar with non-alcoholic Bowser Beer.
Eat: From the Brooklyn Brewery tasting room to local haunts like Drop Off Service, there are over 25 dog-friendly food and drink establishments in New York City. Ride the small dog-approved East River Ferry to Williamsburg, stopping first at Smorgasburg before walking seven minutes to The Levee. Though this is the coolest dog-friendly dive bar in town, offering free cheese balls, cheap drinks, a pool table, and an outdoor space with psychedelic murals, it never feels overrun by the 600,000 dogs that call NYC home.