Hey!
It's a holiday weekend — and that includes your dog.
With Monday off, the city is giving you a proper reason to get out and do something different. Indoor, outdoor, West Village to Astoria — this week has range.
It's also officially rooftop season. A couple of spots around the city are doing holiday weekend drinks up top, dogs welcome. The kind of thing that makes a long weekend feel like it's actually working.
And if you want to make it a proper occasion — there's a flower-filled spring dinner, a block party in Queens, and a Pride photo shoot to close out the weekend. Plenty of reasons to get dressed, get out, and bring the dog.
In this week’s email:
Nice View: Sunset drinks with your best friends and your dog.
Rack ‘em: Bring your good luck charm to this billiards tournament.
Block Party: Summer is officially calling.
Tuesday May 19th
Cellar Dog Billiards Tournament @ Cellar Dog, on Tue, 19 May, 18:30
A proper billiards tournament inside the West Village's massive dog-welcoming game hall — your dog settles in while you run the table. Competitive enough to matter, relaxed enough to enjoy.
Dog Lovers Date Night @ Midtown Manhattan, on Tue, 19 May, 21:00–22:00
A mixer built specifically for single dog parents — the shared context does most of the work before you even arrive. Worth knowing about if your social life and your dog's life have been living separately.
Wednesday May 20th
Wagular Wednesdays @ Sojourn Social, on Wed, 20 May, from 17:00
Every Wednesday this UES bar switches to yappy hour pricing for humans and puts out a barkcuterie board for the dog — the enclosed back patio keeps things contained and the crowd is reliably other dog parents. A standing weekly worth adding to the rotation.
Wooftop Wednesdays @ Rosa's at Park, on Wed, 20 May, 16:00–20:00
The Bronx's only rooftop happy hour built around dogs — drink specials, a dedicated dog menu, and sunset views over Mott Haven. Advance tickets required; spots go fast.
Thursday May 21st
Puppy Party @ JustFoodForDogs, on Thu, 21 May, 18:30
A free weekly trainer-led session for puppies who haven't yet cleared group play — sanitized space, experienced handlers, and a controlled environment that actually builds confidence. Email RSVP required in advance.
Happy Hour @ LoHi Rooftop, on Thu, 21 May, 16:00–20:00
A dog-friendly rooftop in East Williamsburg with covered outdoor seating, city views, and a full bar and kitchen running happy hour until 20:00. A reliable weeknight option that doesn't require a plan.
Watercolor Pet Portrait @ Barking Dog UES, on Thu, 21 May, 17:30–19:30
A one-on-one watercolor session with artist Michele — you dine, you paint, and you leave with a portrait of your dog. Advance registration and a photo of your dog required before attending.
Friday May 22nd
Furry Fridays @ AKC Museum of the Dog, on Fri, 22 May, during museum hours
Every Friday the museum opens to leashed, well-socialized dogs — the current exhibition, Scotland: The Brave Dogs, runs through July 5. Time slots must be reserved in advance.
Yappy Hour @ Tally Ho, on Fri, 22 May & Sat, 23 May, 16:00–20:00
One of the most reliably dog-packed happy hours in the metro area — deeply discounted drinks, dogs welcome, and easy PATH access from downtown Manhattan. Worth the six-minute train ride.
Saturday May 23rd
Spring Fling Dinner @ Boris & Horton, on Sat, 23 May, 19:00–21:00
A flower-filled spring dinner in the East Village with a three-course menu for humans and a matching dog-friendly version for the pup — roasted chicken, strawberry dessert, and a room full of very good dates. The kind of Saturday night that earns the sundress.
Rooftop Drinks @ Westlight, on Sat, 23 May, from 15:00
One of Brooklyn's best rooftops welcomes dogs on both the Turf Club and lower terrace — skyline views across the Manhattan waterfront, recurring every weekend. A strong Saturday afternoon anchor for the Williamsburg crowd.
Sunday May 24th
Smorgasburg @ Prospect Park, on Sun, 24 May, 11:00–18:00
NYC's largest weekly food market — 100+ vendors, a full outdoor bar, and dogs officially welcome at the Sunday Prospect Park location. Note: dogs are not permitted at the Saturday Williamsburg location.
Bark in the Park @ Maimonides Park, on Sun, 24 May, 14:00–17:00
The Brooklyn Cyclones' designated dog sections put you and your dog in seats 22 and 24 — a pre-game pup parade on the field for early arrivals, and a Bark in the Park cap included in every ticket. A Sunday that gives the dog a story.
Monday May 25th
Memorial Day Block Party @ Château Le Woof, on Mon, 25 May, 12:00–sunset
NYC's first dog café kicks off summer with grilled sausages, lobster rolls, and frosé in Astoria. The kind of holiday Monday that actually feels like a holiday.
Through the Lens of Love: Pride Edition, on Mon, 25 May, 15:00–17:00
A pop-up Pride photo shoot celebrating the dog community — bold, inclusive, and benefiting PFLAG. The venue address arrives 36 hours before your shoot; RSVP with payment to secure your spot.
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Have a great long weekend — you and your dog have earned it.
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