Hey!
Last weekend was a mixed bag — but the skies are clearing up, and the timing couldn't be better.
This week is stacked with outdoor options worth actually leaving the house for.
If you want to be social, there are happy hours and rooftops with your dog in the mix. And if this week is about your dog getting their moment — there are a couple of chances to have their portrait done by a real artist.
Indoor or outdoor, people or just the two of you. This week has you covered.
Tuesday May 26th
Pet First Aid & CPR Workshop @ Boris & Horton, on Tue, 26 May, 18:30–20:30
A hands-on class covering CPR, choking, seizures, poisoning, and more — taught by the founder of Waggytail Rescue, who saved a drowning dog from Prospect Park Pond in 2019. Every student leaves with a first aid kit and a certificate.
Sunset Happy Hour @ elNico Rooftop, on Tue, 26 May, 17:00–19:00
A dog-friendly rooftop Mexican restaurant at The Penny Hotel in Williamsburg — both terrace sections welcome dogs, with sunset views across Brooklyn and Manhattan. Food and drink specials run every Tuesday through Thursday.
Wednesday May 27th
Wagular Wednesdays @ Sojourn Social, on Wed, 27 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. No RSVP needed.
Wooftop Wednesdays @ Rosa's at Park, on Wed, 27 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, extended through the end of May. Tickets sell out; advance purchase essential.
Thursday May 28th
Puppy Party @ JustFoodForDogs, on Thu, 28 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. Fills quickly; email RSVP required in advance.
Sip & Paint Party @ The Barking Dog, on Thu, 28 May, 17:30–19:30
Artist Michele Cahill pre-sketches your pet's portrait so you arrive ready to trace and paint — no artistic background needed, just a photo sent in advance. Dogs welcome; pre-registration required.
Friday May 29th
Blue Ribbon Dog Show @ Gallery Onetwentyeight, on Fri, 29 May, 18:00–20:00
A rules-free gallery exhibition celebrating the human-dog bond through painting, sculpture, and portraits — dogs and owners browse together, and artist Eric Ginsburg offers free mini-paintings while supplies last. Final weekend.
Furry Fridays @ AKC Museum of the Dog, on Fri, 29 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, 29 May, 16:00–20:00
One of the most reliably dog-packed happy hours in the metro area — $5 draft pitchers, $7 margaritas, and $1 per pitcher donated to Liberty Humane Society. Easy PATH access from Christopher St, 9th St, or 14th St.
Saturday May 30th
DanceAfrica Outdoor Bazaar @ BAM, on Sat, 30 May–Mon, 1 Jun, 12:00–22:00
The nation's largest celebration of African diasporic dance and music — this year honoring Uganda, with 150+ vendors across food, crafts, and fashion in Fort Greene. Dogs on leash welcome across all three days of the street fair.
Rooftop Drinks @ Westlight, on Sat, 30 May, from 15:00
Both the Turf Club and lower terrace welcome dogs, with unobstructed East River views from one of Brooklyn's most-photographed rooftops. Earlier in the afternoon gives the best combination of space and light.
Mary Jeong Illustration @ Boris & Horton, on Sat, 30 May, 11:00–17:00
Self-taught illustrator Mary Jeong built her practice on pet portraits — starting at 13 with her own dog, Louie — and now creates a broader world of everyday and nostalgic scenes. A Saturday morning reason to stop by the East Village café.
Bushwick Vendors Market @ 87 George St, on Sat, 30 May, 13:00–18:00
A monthly marketplace of 40+ independent artists and makers woven into Bushwick's studio scene — jewelry, art, vintage, food, and handmade goods. Dogs welcome; RSVP in advance for a free prize at the door.
Sunday May 31st
Pupper West Side Street Fair @ Upper West Side, on Sun, 31 May, 12:00–15:00
A neighborhood dog festival on the Upper West Side with organic treat stands, custom dog clothing, rescue booths, and interactive play areas. Exact location confirmed via RSVP.
Smorgasburg @ Prospect Park, on Sun, 31 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. Memorial Day weekend is one of the busiest of the season; arrive early. Note: dogs are not permitted at the Saturday Williamsburg location.
Monday June 1st
Monday Night Jazz & Billiards @ Cellar Dog, on Mon, 1 Jun, 19:00–23:00
NYC's original underground dog-friendly rec room — 9,000 sq ft of pool, ping-pong, shuffleboard, and vintage board games alongside live bebop. Dogs settle into the red leather booths; $5 cover after 18:00.
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Get out there this week — the weather is finally on your side.
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