Love Thyself: A Guide to Self-Pleasure at various locations; 10pm; $40
Inclusive, sex-positive social club NSFW invites members to its Williamsburg clubhouse for a truly hands-on lesson in self-stimulation and, inevitably, satisfaction. Pro sex educators Sir Aaron and Lola Jean show you how loving yourself with patience, practice and creativity makes you a much better lover. It's kind of a win-win.
Tori Amos Barnes & Noble Union Square; 6pm; free with album purchase
The alt-rock goddess speaks about her career and her new album, Native Invader.
Ailey Spirit Week The Joan Weill Center for Dance; 5pm; free
To launch the new wing of its studio, iconic dance institution Alvin Ailey opens its doors for special free editions of its classes. Get a killer workout and learn new skills and styles like hip-hop (October 18 6–7pm), Whine Up: Afrobeat/Caribbean (October 20, 7:30–8:30pm) New York–style mambo (October 21 4:30–6:30pm) and contemporary dance (October 22 2:30–4:30pm), all led by master instructors.
New York Wine Experience Marriott Marquis Hotel; 9am; $375–$2,495
Wine Spectator hosts this annual vino extravaganza, boasting expert seminars, grand tastings and bottle-service luncheons fueled with wines from more than 250 international wineries and châteaus. During the walk-around sampling ($375), sip unlimited wines—all offerings are rated an exemplary 90 points or higher—and chat with the owners and vintners behind the esteemed pours. The pièce de résistance is Saturday's Chef's Challenge, featuring dishes and pairings from megachefs José Andrés, Mario Carbone, Emeril Lagasse and Danny Meyer.
Manhattan Vintage Clothing Show Metropolitan Pavilion; 1pm; $15, at the door $20
This two-day expo is every retro sifter’s dream, featuring more than 80 of the best vintage dealers. As always, you can browse a range of price points starting around $20. The $15 ticket ($20 at the door) is definitely worth it, since you gain access to out-of-towners’ prime goods from the 1900s all the way to the 1990s.
Tompkins Square Park Halloween Dog Parade Tompkins Square Park; noon; suggested donation $5
The Village Halloween Parade is fun and all, but does it have a plethora of puppies in adorable outfits? For that, you’ll have to head to the East Village for this annual dog parade. The getups are remarkably elaborate and conceptual—no surprise given the thousands of dollars’ worth in prizes up for grabs for Best in Show.
Giant Pumpkin Weekend New York Botanical Garden; 10am; Adults $23, seniors and students $20, children (2-21) $10, children under 2 free
Pour out some spiked apple cider for your soon-to-be picked pumpkin homies, which will become the main display at New York Botanical Garden’s pumpkin garden. These monstrous gourds—weighing up to 1,800 pounds—are available for your photo-taking pleasure.
NYC Cupcake Run Astoria Park; noon; $45–$60
Need incentive to get through a 5K? Participants of this race stop to eat cupcakes at three checkpoints along the way, ensuring they can ride that sweet rush all the way to the finish line. If the endorphins and the sugar high don't have you feeling great, this ought to do it: A portion of event proceeds go to nonprofit volunteer organization New York Cares.
Club Cumming The Box; 7pm; $75–$300
Battle of the Sexes and Cabaret costars Alan Cumming and Emma Stone take over the Box at this benefit for Southern Poverty Law Center and Gilda’s Club.
Boo at the Zoo Bronx Zoo Wildlife Conservation Society; 10am; $37
The Bronx Zoo goes all out for Halloween every weekend in October. After a hayride in the haunted forest, catch acoustic performances, beer and food-truck bites at Bootoberfest (noon–4pm), take part in a costume parade (noon–2pm), and face spectral birds of horror lore, including ravens, vultures and owls (11am–3pm).
Crunch Goes Pink 404; 9am; $50
Crunch teams up with the Breast Cancer Research Foundation for its second annual fundraising event. Take your pick of yoga and silent disco–style dance classes, get an onsite massage, peruse health and beauty products, grab a snack from places like Just Salad and Purely Elizabeth and walk out with a complimentary tote bag, tank and towel.
Bonobos Undie Run Pier 40; noon; $20
Bare it all (almost) in support of Fuck Cancer, an organization dedicated to securing equal access to early detection, prevention and support for men's cancers. Raise the most funds and you'll get some free swag, and be sure to stick around after the 2-mile run for an after party with your fellow exhibitionists at Houston Hall. Register here.
SCARE PAIR: Usher House + The Canterville Ghost Kaye Playhouse at Hunter College; 7:30pm; $35
Put some fright in your life with The Center for Contemporary Opera's two-day double bill performance of SCARE PAIR: Usher House + The Canterville Ghost, one-act operas at the Kaye Playhouse at Hunter College that highlight classic elements of Gothic horror. Just in time for Halloween, SCARE PAIR: Usher House + The Canterville Ghost is inspired by Edgar Allan Poe and Oscar Wilde and scored by international composer Gordon Getty.
Tour De Bronx at various locations; 9am; free
New York City’s biggest free cycling event takes over the Bronx with two rides: a 25-mile circuit through the borough’s parks, including Pelham Bay, St. Mary’s and Crotona; or a 40-mile intensive that will take you through City Island, Woodlawn Cemetery, Riverdale and beyond. Post-tour, treat yourself to pizza and live music at a New York Botanical Garden after-party. Check-in at 164th St between Walton Ave and the Grand Concourse.
Madame Morbid’s Trolley Tours Cadman Plaza Park; 4pm, 7pm, 9pm; $69
Hop on a trolley outfitted to look like a Victorian funeral parlor—think chandeliers and velvet curtains—for a trip through the shadows of historic Brooklyn. The tour visits the secret location where Murder, Inc. disposed of bodies, alien abduction sites along the Brooklyn Bridge, a brothel and more. We particularly like the company’s hashtag: #rideordie.