Enjoy exceptional live music on spectacular grounds
Now through August 2; 149 Girdle Ridge Rd., Katonah; (914) 232-5035; caramoor.org
Each summer, Caramoor’s 81-acre Katonah campus bursts into life with music and shared moments under open skies. The 2026 season features over 30 world-class concerts and family-friendly programs. Listeners of all ages are invited to explore, discover and belong. Don’t miss performances by Kelli O’Hara, Hélène Grimaud, Isaac Mizrahi, Patty Griffin, Apollo’s Fire, Punch Brothers, Yuja Wang & People of Earth, Orchestra of St. Luke’s, and full-day American Roots Music and Jazz festivals.
Four reasons to visit ArtsWestchester this summer
Now through August 2: Wed.-Fri. & Sun. 12-5 p.m. + Sat. 12-6 p.m.; 31 Mamaroneck Ave., 3rd fl., White Plains; artswestchester.org/gallery
Looking for something to do today, tomorrow, or any Wednesday through Sunday between now and the beginning of August? Take a trip to downtown White Plains to visit ArtsWestchester’s four exhibits on display through August 2: “Art in a Season of Revolution” showcases artists’ responses to 250 years of American identity; “The Janet Langsam Vault Project” features work by Rana Amirtahmasebi inspired by her Iranian background; photography by Chimoa Nwana depicts the oldest Black churches in White Plains; and the LGBTQ+ Listening Library features music from LGBTQ+ artists. Visit artsw.org for more information.
Spend the summer enjoying a microwinery right in our own backyard
Thurs.-Sat. 7:30 a.m.-7 p.m. & Sun. 7:30 a.m.-5 p.m.; 1202 Route 35, South Salem; southsalemwinery.com
Vintner John Vuolo has spent decades crafting wine using old-world techniques, and now he’s brought his expertise to South Salem Winery. Using grapes sourced from small vineyards on the North Fork of Long Island, all wines are crafted in house. Located inside the greenhouse at Gossetts Nursery, South Salem Winery has partnered with CIA-trained chef Tracy Assue to offer delicious in-house baked goods with your wine. Stop by for a tasting and leave with a bottle (or two).
Explore perception, gesture, and the psychology of color
May 2: public reception, 4-6 p.m.; May 2-June 13: exhibition, 10:30 a.m.-5:20 p.m.; 382 Greenwich Ave., Greenwich; heathergaudiofineart.com
Heather Gaudio Fine Art presents “Patrick Alston: Apertures,” his first solo exhibition at the gallery. “Apertures” builds on an understanding of perception as something both deeply personal and collectively shared, shaped through gesture, color and accumulated layers that hold traces of time, decision and revision. These echo philosopher Alan Watts’ metaphorical philosophical statement, “You are an aperture through which the universe looks out.” The show opens with a public reception on May 2 from 4 to 6 p.m. and runs through June 13.
We give you permission to laugh that hard
May 8: Captain Lawrence Mount Kisco, 7 p.m.; May 15: Sunflower of Westchester fundraiser, 8 p.m.; June 5: The Lark After Dark, 8 p.m., 50 S. Buckhout St., suite G107, Irvington; June 7: “Nothing to Luz,” St. Marks Comedy Club, 7 p.m., 12 St. Marks Pl., NYC; June 12: The Lewisboro Library, 8 p.m.; @hardheadedcomedyinc; campsite.bio/hardheadedcomedy; nothingtoluz.com
At Hard Headed Comedy, we believe laughter is the best medicine—no copay, no waiting room, just pure joy. It’s not just entertainment—it’s therapy with punchlines. Founded by the unapologetically bold Luz Michelle, Hard Headed Comedy brings inclusive, high-energy shows to the greater Westchester area, creating spaces where humor heals and connection thrives. Follow us @hardheadedcomedyinc for show updates, behind-the-scenes fun, and your weekly dose of laughter—side effects may include happiness. And be part of Luz’s comedy album recording—her first in over 15 years: “Nothing to Luz,” live on June 7 at 7 p.m.
Which Mom do you have? A drag bingo mom or a murder mystery mom?
May 10: Mommie Dearest Drag Bingo, 12 p.m., Mommy, Fearest Murder Mystery, 6 p.m.; 56 Pole Bridge Rd. Sandy Hook, CT; aquilasnestvineyards.com
Aquila’s Nest Vineyards, an award-winning 41-acre winery and event estate in Sandy Hook seamlessly blends Mediterranean heritage, mythology, wine and sweeping sunset views into an immersive guest experience. Known for its dynamic calendar of live music, tribute performances, curated tastings, gourmet pairings, and seasonal offerings, the vineyard has become a beloved destination for celebration. This season, Aquila’s Nest will also present several Mother’s Day events, offering families memorable ways to honor and celebrate together.
Food trucks, finish lines and frosting
May 15, June 12, July 17, Aug. 14 & Sept. 18: Food Truck Fridays, 5-9 p.m. in Scotts Corners, Pound Ridge; May 31: Color Run, 9 a.m. at Pound Ridge Elementary School; June 13: Bake-off Challenge, judging at 10 a.m. at Pound Ridge Green; June 21, July 19, Aug. 16: Music on the Green at Pound Ridge Green; poundridgepartnership.org/events
Celebrate community spirit in Pound Ridge with this spring/summer’s can’t-miss events. Starting on May 15, feast at Food Truck Friday with multiple delicious trucks, live music and family fun. Then, on May 31, lace up for the colorful Pride-inspired 5k Color Run and Fun Run. And don’t forget to show off your baking skills (or come to watch) on June 13 at the Bake-Off Challenge, featuring cakes, cookies and pies made by your neighbors who have agreed to subject themselves to live judging. And enjoy music on the green in June, July & August (rain date: Sept. 20).
Meet you at the Dragon Coaster
May 16-September 13: Playland Park, 1 Playland Pkwy., Rye; (914) 813-7010; playlandpark.org
Make memories that last a lifetime at Playland Park in Rye. From classic rides the whole family loves to unforgettable twists and turns for your growing thrill-seekers, there’s something for everyone. Take a spin on timeless favorites like the Grand Carousel and enjoy a day full of games, food and fun! For park hours, fees and tickets, visit playlandpark.org.
Kayah, Sup, with Hudson River Expeditions
May 23–mid-Oct: Beacon, Cold Spring and Staatsburg; hudsonriverexpeditions.com
Some of the best views in the Hudson Valley don’t require hiking boots. Paddle past Bannerman Castle, watch the sun set over the Hudson Highlands from your kayak, or wake up on an island in the middle of the river. We offer guided kayak tours including twilight, history, waterfall, Paddle & Paint, and more, plus ACA-certified instructors and kayak and stand-up paddleboard rentals in Beacon and Cold Spring. August Kids’ Kayak Camps and corporate and private events available. First time on the water or seasoned paddler, there’s a program for every level.
Visit Ireland (in North Salem) via The Schoolhouse Theater
May 15-31: North Salem Community Center, 3 Owens Rd., Croton Falls; theschoolhousetheater.org
In a quiet corner of rural Ireland, two stubborn souls circle each other with equal parts pride, fear and longing. “Outside Mullingar” is a deeply funny and unexpectedly moving romance about missed chances. With Shanley’s signature wit and warmth, what begins as gentle comedy blooms into something quietly profound. You’ll laugh, you’ll ache and you may just believe in love a little more than you did before. Tickets can be purchased on the website.
Celebrate legendary Bedford residents who saved millions of lives
June 6: picnic (in person: 11 a.m., virtual: 1:45); June 4-6, 7 p.m. & June 7, 1 p.m.: “Bill & Lois Wilson: In Their Own Words” (play), Bedford Hills Community Center; June 7, 9:30 a.m., “Bill W. Conscious Contact” documentary & meditation, Bedford Playhouse; steppingstones.org/events
Learn more about Bill & Lois Wilson, Bedford residents and founders of AA & Al Anon (which is 75 years old this year) by doing one of the following: Get tickets to attend the 75th annual picnic in Bedford (or attend virtually). Watch their love story come to life in a professional production of “Bill and Lois Wilson: In Their Own Words,” from Katonah Classic Stage, supported by a grant from THRIVE. Or, watch the documentary “Bill W. Conscious Contact” at The Bedford Playhouse, followed by a meditation and Q&A with the producer.
A triathlon just for kids? Yes, and it’s local.
June 7: 8 a.m.; 60 Haines Rd., Bedford Hills; trisignup.com/race/ny/bedfordhills/trithepark
NeverStopMoving’s second TRI the PARK is a youth triathlon designed for fun, challenge and community spirit. Held at Bedford Hills Memorial Park, participants between the ages of 6-16 will compete in a pool swim, followed by a park bike and run. The entire race should take athletes anywhere from 10 to 30 minutes, and each participant will receive a finisher’s medal. Participants can compete in either the long course or the short course. Registration closes on May 31. Can’t make the local one? There’s another race in Tarrytown on July 19 (registration closes on July 12). Check out trisignup.com/race/ny/tarrytown/tritheparktarrytown for more information.
Meet your new favorite wellness routine
June 13: 10 a.m.-2 p.m.; Village Hall, 104 Main St., Mount Kisco; mtkiscochamber.com
Join the Mount Kisco Chamber of Commerce for the inaugural Kisco Wellness Fair on the grounds of Village Hall. At this free open-air event, you can meet local health and wellness professionals, explore the numerous wellness options available, learn from free demonstrations and enjoy complimentary open-air fitness classes—all designed to help you get moving, reach your wellness goals and become your best self. Then, spend Wellness Week (through June 20) at these establishments, using the specials and promotions you received at the fair. Plus, enter for a chance to win one of multiple prizes from local wellness businesses.
Salsa, Zumba, concerts and art all summer long
June 14-Aug. 9: Cross County Center, 8000 Mall Walk, Yonkers; crosscountycenter.com/events
Cross County Center’s Summer Fest 2026 brings the season to life starting on Sunday, June 14 through Sunday, August 9 (pending rain delays), featuring free family fun all summer long. From live concerts and Zumba classes to salsa nights and kid-friendly activities from ArtsWestchester, this is when “there’s something for everyone” is actually true. Plus, there’s shopping, dining and free parking. It’s Westchester’s go-to destination for unforgettable summer evenings (or afternoons for art).
Be in the room where the revolution happened
June 19-21 & June 25-28: Bedford Historical Hall, Bedford Village; bedfordny.gov/1891/Events
Immerse yourself in the only local staging of the Tony Award-winning musical “1776,” presented as part of Bedford Rev Up 250. Set inside the Bedford Historical Hall, this site-specific production places audiences among America’s founders as they debate independence. Nearly a decade after their original acclaimed production, director Mitch Horn and producer Stephanie McCaine reunite to bring this powerful production back to life.
Sports, adventure, swimming & the arts—all in one camp
June 29-August 21: 825 Union Valley Rd., Carmel; kiwicountrydaycamp.com
Kiwi Country Day Camp offers a fun, traditional summer experience for children ages 3–15. Campers spend their days outdoors building friendships, exploring new activities and heading home happy, tired, and more confident than when they arrived. Conveniently located in New York just off Route 684, with transportation available throughout Westchester and Fairfield counties, Kiwi blends classic camp spirit with today’s highest safety standards—creating an unforgettable experience for kids and peace of mind for parents.
Free live music, great local food and you can even bring your friends
July 11, 18 & 25 and August 1 & 8: Gazebo at Wampus Brook Park, 6-8 p.m.; 4 Maple Ave., Armonk; armonkchamberofcommerce.com/summer-concerts
Starting on July 11 for five straight Saturdays, North Castle Parks/Rec and the Armonk Chamber of Commerce invite you to enjoy free live concerts at the Gazebo in Armonk. Featuring music from Nashville, Springsteen, Fogerty and others. Bring your lawn chairs, grab a bite from one of the nearby restaurants and come to relax and enjoy live music. Concerts begin at 6 p.m. and go until 8 p.m. Need more music? We’ve also got concerts from June 24 through September in Armonk Square.
“Here it goes again,” for the 20th year in a row
July 11: gates open at 11:30 a.m., music starts at 12:30 p.m.; Parkway Field, Pleasantville; pleasantvillemusicfestival.com
Dust off your treadmills and get ready for confetti cannons with thousands of your closest friends/fellow music lovers at this year’s Pleasantville Music Festival. It’s a day of world-class music, food, drinks, kids’ activities and crafts. Plus meet local charities and feel good about attending a zero-waste festival. This year’s lineup includes our favorite treadmill-dancing alt. rock group OK Go, the witty country-esque tunes of Old 97’s, new wave synth icons The Fixx (of “One Thing Leads To Another” fame), the gritty, soulful The Vindys, garage rock band The Thing, and more. Get your tickets before the July 5 price increase.
Blues + BBQ + Puppies = A perfect Sunday in July
July 12: Blues & BBQ, 4–7 p.m.; Bedford Memorial Park, Bedford; bedfordarmonkrotary.org
What are you doing on July 12? Not sure yet? We have your answer. You’re heading to Bedford Memorial Park that afternoon for the annual Bedford-Armonk Rotary and Lions Club’s “Blues and BBQ” event. Enjoy a fun family-and dog-friendly event, catered by Billy Fortin of Scott’s Corner Market in Pound Ridge and featuring live music, dancing, face painting, balloon animals and more. Bring a blanket/folding chairs or whatever will make you most comfortable. Rain or shine.
Kids need to brush up on their baseball skills? You’re JustinTime.
JustinTime Baseball aims to cover all facets of the game. Our public programs provide structured training in a fun, high-energy environment. Whether your child is just starting or looking to refine their skills, we have the right program for everyone. We provide a fun environment where kids can honestly learn, grow beyond the game, and build confidence. Register on our website, and we will see you on the field this spring and summer. Visit our website for details.
The editorial staff at Connect To magazine.
