Created by Steve Dean Updated On: August 5, 2019
The best damn walking date you'll ever go on. 7-9+ hours, 5+ miles of walking, ample time for conversation, beautiful photo ops, tasty coffee & small bites, and amazing live shows | Dateworking.com
Steve Dean: Great for powering up to start your day. They've got lots of protein packed snacks for a day of walking. Ask to try their ultra flavorful natural processed coffee if they've got it in stock!
Steve Dean: One of NYC's most iconic landmark and at one point the tallest structure in all of Manhattan, the Brooklyn Bridge is now a touristy clusterfuck but is undeniably gorgeous. B-Y-O-Selfiestick.
Steve Dean: A much more peaceful walk than the Brooklyn Bridge thanks to the dedicated pedestrian path not shared with bikers. This bridge is a photographer's dream -- try to count the holes cut into the fence!
63 Flushing Ave (btwn Navy St & Clinton Ave), Brooklyn, NY
Historic and Protected Site · Brooklyn Navy Yard · 20 tips and reviews
Steve Dean: If you can't snag a tour of the Brooklyn Grange Rooftop Farm, you can always hang out in the air conditioned rooftop cafe next door at Building 92, home of the navy yard museum. Reup on caffeine here!
Steve Dean: If you're lucky, you can snag a free tour, and get to see the beekeepers in action. Don't forget to take advantage of the rooftop views of Manhattan!
Steve Dean: My favorite game: try to count the # of dogs vs. the # of kids in strollers. Make sure you get selfie together from beneath the Williamsburg Bridge.
Steve Dean: Easily the best graffiti of any of the bridges I've encountered in NYC, and by far the nicest bridge to walk along, given the lack of bikes and the relative lack of tourists. Tons of native NY'ers!
Empanada Restaurant · Lower East Side · 35 tips and reviews
Steve Dean: Having walked 3 bridges and many miles, you'll have surely worked up an appetite by now, so grab a quick, but filling bite here before you start drinking. Try the viagra empanada. You won't regret it.
168 Delancey St (btwn Clinton & Attorney St), New York, NY
Lounge · Lower East Side · 103 tips and reviews
Steve Dean: Famous for its foliage-filled rooftop bar where you can steal away for a private moment of conversation while overlooking the streets at the heart of NYC's Lower East Side.
172 Rivington St (Attorney and Clinton), New York, NY
Coffee Shop · Lower East Side · 61 tips and reviews
Steve Dean: A great spot to watch some experimental comedy or poetry readings each night, plus they serve wine, beer, tea, and coffee, so you're covered no matter what mood you're in.
Performing Arts Venue · Lower East Side · 15 tips and reviews
Steve Dean: NYC's most iconic spot for "intellectual nightlife," Caveat features 2 live shows every night of the week, ranging from "Why Your Train Is F*cked" and "Anybody: a Hamilton-inspired hip hopera."
Hester St (btw Chrystie & Forsyth St), New York, NY
Playground · Lower East Side · 15 tips and reviews
Steve Dean: If you're exhausted from your journey and need a good spot to simply lay on your backs and watch the stars, wander down to the Hester St. Playground track by Canal Street. Chill AF on summer nights.