Planning a girls’ night out in Westchester shouldn’t require a group chat with 47 messages and zero decisions made. We’ve done the legwork. We’ve shown up to places with groups of 6, 10, sometimes 15 women and figured out which spots actually work versus which ones sound great until you’re standing in a cramped lobby being told the wait is two hours.
Here’s where to go, organized by what kind of night you’re in the mood for.
Cocktail bars and wine bars worth the drive
The Chestnut in Dobbs Ferry is our go-to when the group wants craft cocktails without pretension. The bar area is big enough that you can actually stand together and talk without screaming. They do seasonal menus and the bartenders are genuinely good at what they do. Street parking can be rough on weekends, so rideshare or take the Metro-North to Dobbs Ferry station (it’s a five-minute walk).
Purdy’s Farmer & the Fish in North Salem has a bar scene that picks up nicely on Thursday and Friday nights. The space is gorgeous and the drinks are solid, but fair warning: this one works better for groups of 4-6. Show up with a dozen people and you’ll be scattered across the room.
Teeth in Tarrytown is a cocktail bar with a darker, moodier atmosphere. Small plates, interesting drinks, and a space that feels more Brooklyn than Westchester. Reservations are smart here, especially Fridays and Saturdays. Groups over 6 get tricky because the space is intimate, so plan accordingly.
For wine bars, Village Wine in Pleasantville lets you do self-pour tastings, which is honestly the most fun a group of women can have standing up. You get a card, you try what you want, nobody has to agree on a bottle. They also have cheese boards. Parking lot right there.
The Tasting Room in Port Chester is another strong pick. It’s got a big enough space for groups and the wine list is extensive without being intimidating. Port Chester in general is underrated for a night out because there’s plenty to walk to if you want to bar-hop.
Dinner spots that can actually handle your group
This is where most girls’ night out plans fall apart. You pick a restaurant that looks amazing, call to make a reservation for 9, and they tell you the biggest table seats 6. Here are places that won’t do that to you.
Rosemary & Vine in Rye does a great job with larger parties. Mediterranean menu, lots of shareable plates, and the vibe is lively without being so loud you can’t hear the person across from you. Make a reservation at least a week out for groups of 8 or more.
The Cookery in Dobbs Ferry has a private dining area you can reserve for bigger groups. The food is farm-to-table and consistently good. This is the spot when you want dinner to feel like a real occasion. Metro-North accessible from the Dobbs Ferry stop.
Ernesto’s in White Plains is a reliable Italian spot where the portions are huge and they’re used to handling large groups. Nothing fussy, just really solid food and a staff that doesn’t make you feel like your party of 12 is an inconvenience. Parking garage nearby on Mamaroneck Ave.
Mission Taqueria in New Rochelle brings the energy. Great tacos, strong margaritas, and a restaurant that gets loud and fun as the night goes on. They can accommodate bigger groups but you should call ahead. This is the pick when the group wants something less “nice dinner” and more “let’s have a night.”
Lola’s Mexican Kitchen in Hastings-on-Hudson is perfect for the group that wants guacamole made tableside and a margarita pitcher. Smaller space, so keep your party under 8 here. Right off the Hastings Metro-North stop.
Paint nights, pottery, and crafting that’s actually fun
The paint-and-sip formula works because it gives everyone something to do besides stare at their phones, and you leave with a thing. Some of these have gotten stale, though, so here are the ones worth booking.
AR Workshop in Scarsdale goes beyond painting. You can do wood signs, canvas totes, and other projects that don’t all look the same. They run private group sessions, which is the way to go. Book early because weekend slots fill fast.
Color Me Mine in Scarsdale and Larchmont is the classic paint-your-own-pottery setup. Yes, it’s been around forever. It’s still fun, especially when half the table is competitive about their mug glazing. No reservations needed for small groups, but call ahead if you’re bringing more than 6.
Board & Brush in Armonk does the rustic wood sign thing and they’re good at it. BYOB at most of their events, which immediately makes any craft night better. Private parties available if you’ve got a birthday or just want the space to yourselves.
Cooking classes for the group that’s over bar hopping
Zwilling Cooking Studio at their headquarters in Pleasantville is honestly one of the most underrated group activities in Westchester. Professional-grade kitchen, actual chef instruction, and you eat everything you make. They do themed classes (pasta making, sushi, seasonal menus). Book a private class for your group if you can swing it. This is the one people talk about for weeks after.
Sur La Table in Westchester (The Westchester mall in White Plains) runs group cooking classes too. More accessible price point and they handle larger groups well. The classes are structured so even the person who burns toast can participate without stress.
Karaoke, bowling, and games
Sometimes the group doesn’t want to sit down at all. Sometimes the group wants to sing Shania Twain badly and loudly.
Grand Prix New York in Mount Kisco has go-kart racing, bowling, and an arcade. It sounds like a kids’ birthday party until you’re racing your friends at 45 mph and talking trash. They have a full bar. Friday and Saturday nights get busy, so book your lanes or race times online.
Bowlero in White Plains (and other Westchester locations) is the obvious bowling pick, but it works. Glow bowling on weekend nights, decent food, full bar. Easy to book for groups and nobody cares if you’re terrible.
For karaoke, your best bet is heading to Port Chester. Patio PK does Korean BBQ and has private karaoke rooms, which is really the only way to do karaoke. Nobody wants to sing in front of strangers. Private rooms mean your group can be as loud and off-key as necessary. Reserve a room in advance.
Comedy and live shows
The Loft at City Limits in White Plains books stand-up comics regularly, including touring headliners. It’s a proper comedy club setup with a two-drink minimum, and the shows are genuinely funny. Tables seat groups well. Friday and Saturday shows sell out, so buy tickets early.
Lucy’s Lounge in Pleasantville is a dive bar that hosts live music, comedy nights, and open mics. It’s small and no-frills, but the programming is surprisingly good and the drinks are cheap. Not the spot for a group bigger than 6 or 7 unless you’re fine being spread out.
Seasonal stuff you should actually do
Westchester Magazine’s Wine & Food Festival happens annually and it’s a great group outing. You walk around, sample from local restaurants and wineries, and nobody has to agree on where to eat. Buy tickets the day they go on sale because they sell out.
Hudson Valley Shakespeare Festival does outdoor summer performances that make for a genuinely great evening out. Pack a picnic, bring wine, sit on a blanket. It’s in Garrison, which is technically Putnam County, but it’s close enough and too good to skip.
In fall, harvest festivals and cideries are everywhere. Harvest Moon Farm & Orchard in North Salem and Hilltop Hanover Farm in Yorktown Heights do events through the season. Pair a farm visit with dinner at a nearby restaurant and you’ve got a full night.
Winter holiday markets pop up across the county in November and December. Westchester’s Winter Wonderland at Kensico Dam Plaza in Valhalla has ice skating, lights, and vendors. It’s cheesy and fun and perfect when the group includes people who “don’t drink.”
A few practical notes
Reservations: Any restaurant in this list, for a group of 6 or more, needs a reservation. Don’t wing it. Call at least a few days out, a week for weekends.
Metro-North: If you’re going out in Tarrytown, Dobbs Ferry, Hastings, Pleasantville, or White Plains, take the train. Nobody wants to figure out parking after two glasses of wine, and nobody wants to be the designated driver. The Harlem and Hudson lines run late enough on weekends.
Rideshare: Works great in southern Westchester. Gets spottier the further north you go. If you’re heading to North Salem or Armonk, coordinate rides.
Port Chester deserves a special mention as the best walkable night-out neighborhood in Westchester. Restaurants, bars, and music venues are all within a few blocks. Park once, walk everywhere.
Or just let someone else plan it
This is literally what Club West does. We put together group nights out so you don’t have to be the one sending “does Thursday work??” to 12 people for three weeks straight. Check our upcoming events for the next one, or sign up if you’re not a member yet and want in.
Hours, menus, and reservation policies change. Check directly with any venue before showing up with your crew.