Summer is in full swing in Upper Westchester, and there’s no better time to explore the best our beautiful county has to offer. From twilight firefly walks and jazz in the garden to bustling farmers markets and sizzling food truck nights, consider this your invitation to step outside and savor the season with purpose and pleasure.
Whether you're a nature lover, music buff, or a family on the hunt for easy weekend outings, here are 10 must-do experiences to help you live your best summer life:
1. Feed Your Senses at Blue Hill at Stone Barns
July 26 & August 23 – Market Days
Wander through the fields and learn about regenerative agriculture while sampling peak-season produce and pantry goods at Market Days on the Stone Barns campus.
August 3 – Fresh & Dried Flower Workshop
Join the Crops Team to handcraft your own bouquet with freshly harvested and dried blooms.
July 5 & 6 – Firefly Walk & Dinner at Community Table
Book an early dinner at the Community Table, then enjoy a magical nighttime walk led by Ecological Monitoring Director Elijah Goodwin. Watch fireflies light up the fields and learn how nocturnal creatures interact with this thriving, biodiverse landscape.
2. Bask in the Sounds of Summer at Caramoor in Katonah
Caramoor’s open-air grounds offer a magical setting for unforgettable performances and family-friendly experiences.
July 4 – Pops, Patriots & Fireworks
Celebrate Independence Day with a stirring concert by the Westchester Symphonic Winds and a dazzling fireworks finale.
July 6 – Afternoon Tea in the Music Room
Sip Harney & Sons tea in one of Caramoor’s most beautiful historic spaces, served with tea sandwiches, scones, and desserts.
July 26 – Caramoor Jazz Festival
Co-presented with Jazz at Lincoln Center, this all-day festival features live music throughout the gardens, culminating in a performance by Arturo O’Farrill & the Afro Latin Jazz Orchestra.
3. Score a Summer Steal at Katonah Sidewalk Sale Days
July 18–19
Stroll downtown Katonah and shop locally at this beloved annual event. Grab an iced latte, pop in and out of charming boutiques, and enjoy exclusive discounts from your favorite neighborhood spots.
4. Rock Out at the Free Robison Summer Concert Series
Kensico Dam Plaza, Fridays in July
Pack a picnic and dance under the stars at this family-friendly concert series. This year’s lineup includes crowd-pleasers like:
-
July 11 – The Great American Soul Book
-
July 18 – The Jersey Tenors (Frankie Valli to Sinatra)
-
July 25 – Love Story: A Taylor Swift Tribute
5. Savor Food Truck Fridays in Pound Ridge
July 18, August 22 & September 12: 5–9pm
This monthly tradition brings gourmet eats, live music, and a laid-back community vibe to Scotts Corners. Come hungry!
6. Stroll & Shop at Northern Westchester’s Best Farmers Markets
There’s no better time to enjoy locally grown produce, fresh flowers, handmade goods, and neighborly vibes.
-
Sundays – Honeybee Grove Flower Farm (June–October)
-
Sundays – Muscoot Farm Market (May–November)
-
Saturdays – Gossett’s Farmers Market (Year-round)
-
Saturdays – John Jay Homestead Farm Market in Katonah
7. Unwind at Armonk’s Summer Concerts at the Gazebo
Settle into a lawn chair with a cold drink and soak up the sounds of live local music in the charming setting of Wampus Brook Park. You’ll also find performances popping up in the town square throughout the summer. Visit the town website for the full Music in the Square schedule.
8. Go Wild at Muscoot Farm
This working farm and nature preserve in Katonah is a summer staple. Beyond its weekly market, kids and adults love saying hi to their resident barnyard animals, exploring the walking trails, and joining in on seasonal events hosted throughout the summer.
9. Explore Local Nature on a Guided Walk with Lewisboro Land Trust
Get to know the natural beauty of Northern Westchester through free, family-friendly hikes hosted by the Lewisboro Land Trust. From scenic meadow strolls to toddler-friendly adventures, these guided outings are a fun and educational way to connect with nature, learn about native wildlife, and meet neighbors who share a love for the outdoors. Visit their website for the full schedule of summer walks and special events.
10. Celebrate Community at Destination 39.3’s Bedford Music Festival at Caramoor
September 13, 2:00pm
Close out the season with live music, delicious food, and community spirit at this all-ages festival, featuring Big Head Todd and the Monsters. Hosted on the Caramoor grounds for the first time ever, this festive day promises an unforgettable sendoff to summer.
Westchester’s warmest days are made for local adventures...so grab your sunhat, round up your crew, and start exploring!