There’s something about fall that invites reflection, reinvention, and road trips. The crisp air, golden leaves, and cozy vibes make it the perfect season to explore somewhere new—or somewhere that feels like a soulful homecoming. For me, that place is Pawling, New York.
I first discovered Pawling through my love of Daryl Hall and his iconic show Live from Daryl’s House. Every time I tune in, I am captivated—not just by the music, but by the intimate, rustic charm of the venue itself. And when I learned that Daryl’s House Club was a real place nestled in the Hudson Valley, I knew I had to go. So Pawling is now on my bucket list… it’s rich history, nature, and creativity—make it a perfect fall destination for women who crave inspiration and adventure.
A Town Steeped in History and Natural Beauty
Located in Dutchess County, just 65 miles north of New York City, Pawling is a picturesque village with deep colonial roots. It played a role in the Revolutionary War and was once home to legendary broadcaster Lowell Thomas, whose memorabilia is housed in the historic John Kane House.
John Kane House
Other historic gems include:
- Oblong Friends Meeting House – A Quaker landmark dating back to the 18th century.
Oblong Friends Meeting House
- The Book Cove – A charming independent bookstore perfect for cozy fall browsing.
- Lakeside Park – Ideal for leaf-peeping and peaceful walks.
And for nature lovers? The Pawling Nature Reserve and Appalachian Trail offer breathtaking hikes through forests ablaze with autumn color.
Daryl’s House Club: Where Music Meets Magic
Of course, no visit to Pawling is complete without a night at Daryl’s House Club—a rustic restaurant and live music venue founded by Daryl Hall himself. It’s intimate, welcoming, and packed with talent.
Daryl’s House Club
Over the years, the stage has hosted legends and rising stars alike, including:
- David Cook
- Lisa Fischer
- The Smithereens
- Kris Allen
- Sonny Landreth
- Sawyer Fredericks
This fall, the lineup is electric. Upcoming headliners include:
- Eric Hutchinson (Nov 22)
- Anthony Gomes (Nov 19)
- Roomful of Blues (Nov 7)
- Morgan James (Nov 2)
- Greg Raposo (Oct 19)
- L.A. Guns (Oct 8)
- Chuck Prophet (Sep 18)
- David Cook (Sep 17)
Whether you’re into blues, rock, country, or tribute bands, there’s something for every music lover—and the food and ambiance make it a full sensory experience.
Auling Station
Local Finds and Cozy Moments
Beyond the music and trails, Pawling offers delightful shops and galleries:
- Live 4 Art Gallery – Featuring local artists and artisan gifts.
- Land Gallery – Known for fine landscape photography.
- Pawling Tavern – A lively spot for post-concert drinks.
And if you’re planning a weekend escape, nearby inns and B&Bs offer warm hospitality and scenic views.
Why Pawling Speaks to the Soul
As a woman who celebrates reinvention, creativity, and connection, Pawling feels like a mirror to my own journey. It’s a place where history meets harmony, and where every trail, tune, and conversation feels intentional. Whether you’re hiking solo, dancing at Daryl’s, or sipping cider by the fire, Pawling invites you to slow down, tune in, and fall in love with the moment.
Your Turn
Have you ever visited (or have on your bucket list) a place that felt like it was calling your name? What’s your favorite fall destination—or dream concert venue? Share your thoughts with us at WE Magazine or tag us in your Pawling adventures. And if you’re a fellow Daryl Hall fan, let’s swap favorite episodes!
Cover Image Akin Library
All images source: Wikipedia
