Hi all,
Greetings from poolside at Prospect Berkshires, where I spent most of this week photographing the property. Though it’s in Massachusetts — not Upstate — it’s no farther than many of the places we feature, sitting less than 150 miles from New York City. And what a world away! At check-in, you park your car and are whisked away by golf cart through the woods to a former summer camp turned design hotel. The food, staff, pool, cabins, and many saunas are all exceptional. I’m already planning a return trip for a personal stay (no camera, no work allowed) for some pool, sauna, tennis, and lake time.
As a reminder, Prospect Berkshires is one of our July Escape Club partners, offering members 25% off Sunday–Thursday stays through the end of 2026. I can personally confirm that midweek is especially lovely, when the property feels peaceful and uncrowded.
This week we’re also highlighting Seminary Hill, where summer programming now includes a partnership with Landers River Trips — a pretty perfect way to spend a day on the Delaware River, whether you prefer tubing, kayaking, canoeing, or rafting. (I’m partial to the tube. Keep an eye out for bald eagles!) Escape Club Members can save 25% on two-night stays through the end of September.
Below, you'll also find three very different real estate listings: a handcrafted Cape near the Ashokan Reservoir, a designer-restored landmark in Franklin, and Rockbound, the beautifully restored former caretaker's residence and carriage house of the Filer/Guggenheim Estate. Dig in, and have a great weekend!
See you out there,
— Erin
Founder & Creative Director, Escape Brooklyn
Perched above the Delaware River Valley, Seminary Hill is a working orchard and cidery whose hilltop campus is home to a MICHELIN Key-awarded hotel, destination restaurant, and tasting room overlooking the surrounding hills. Guests stay in The Boarding House, where eight thoughtfully designed apartments ranging from one to four bedrooms make it an easy getaway for couples, friends, and families alike.
This summer, guests can book Seminary Hill’s signature Cider Experience, which includes a guided orchard and cidery tour, two bottles of cider in-room, a $50 restaurant credit, and early check-in and late checkout. (Book here and choose “Cider Experience” rate)
Looking to cool off? Seminary Hill guests also receive 15% off tubing, kayaking, canoeing, and rafting with nearby Landers River Trips — one of our favorite ways to spend a summer afternoon on the Delaware River.
Between mornings exploring Callicoon’s charming Main Street, afternoons on the river, and evenings overlooking the orchard with dinner and cider, Seminary Hill makes it remarkably easy to build an entire summer weekend without driving very far at all. Read our full Seminary Hill feature on Escape Club.
🔐 Escape Club Members Save: Receive 25% off 2-night stays through September 30. Click the button above to unlock the member discount.
Built in 1878 as Franklin’s original bank and post office, this remarkable Main Street landmark has been thoughtfully restored by acclaimed designers Sean Scherer of Kabinett & Kammer and fashion designer Gary Graham.
The result is a one-of-a-kind mixed-use property that balances historic preservation with contemporary living, bringing together beautifully restored commercial spaces, a private residence, artist studio, and income-producing apartment beneath one roof.
Set in the western Catskills, Franklin has quietly become a destination for artists, designers, and creative entrepreneurs drawn to its beautifully preserved Main Street and strong sense of community, all less than three hours from New York City. View the full listing here.
Originally built in 1878 as Franklin’s original bank and post office | Three bedroom, three full and two half bathroom designer-restored mixed-use landmark | 5,262 square feet | Two restored storefronts | Loft-style artist studio | Designer residence | Income-producing apartment | 2 hours, 45 minutes from NYC | Asking $645,000
Listed by Sarah Broach of The Way We Live Team at Compass and Deb Dolan of Keller Williams Upstate NY. For showings and inquiries, contact Sarah at sarah.broach@compass.com, (917) 535-1127; or Deb at deb-dolan@kw.com, (607) 544-4062.
Set down a long driveway just minutes from the Ashokan Reservoir, this custom-built Cape is surrounded by 3.7 private acres of mature woodland and gardens.
Built with an appreciation for traditional craftsmanship, the home features locally sourced heart pine floors, antique chestnut post-and-beam construction, reclaimed tobacco barn oak, custom-built cabinetry, and a high-efficiency wood stove framed by a stone surround built from rock gathered on the property.
Outside, established pollinator gardens, a greenhouse, and a detached insulated studio extend the living space beyond the house, creating a peaceful retreat just minutes from Kingston, Woodstock, and the Ashokan Reservoir. View the full listing here.
Three bedroom, two bathroom custom-built Cape on 3.7 private acres | 1,920 square feet | Locally sourced wide-plank heart pine floors | Antique chestnut post-and-beam construction | Reclaimed tobacco barn oak floors | Custom-built cabinetry | High-efficiency wood stove with stone surround | Greenhouse and private deck off the primary suite | Detached insulated studio with electricity | Asking $849,000
Listed by Theodore Chazkel of Four Seasons Sotheby’s International Realty. For showings and inquiries, contact Theodore at (845) 594-5477 or theodore.chazkel@fourseasonssir.com.
Open house: Sunday, July 12, 2026 from 1:00–3:30 PM at 323 Beaverkill Road, Kingston, NY 12401. RSVP using the contact information above.
Set on 3.2 acres within the former Filer/Guggenheim Estate in Orange County, Rockbound is a thoughtfully restored historic residence where more than a century of craftsmanship has been carefully preserved alongside contemporary updates.
Originally built as the estate’s caretaker’s residence and carriage house, the two buildings have been joined into a single home through a meticulous six-year renovation that honors the property’s architectural history while introducing modern comforts throughout.
Original wide-plank floors, hand-hewn beams, antique windows, stone fireplaces, a heated saltwater pool, and beautifully preserved outbuildings — including the original ice house and smokehouse — create an exceptional balance of history and modern living just one hour from NYC. View the full listing here.
Four bedroom, three-and-a-half bathroom restored estate residence on 3.2 acres | Originally the caretaker’s residence and carriage house of the former Filer/Guggenheim Estate | 4,697 square feet | Six-year restoration preserving original wide-plank floors, hand-hewn beams, antique windows, and stone fireplaces | Chef’s kitchen with deVOL fixtures, heated European limestone floors, soapstone island, and professional six-burner range | Heated saltwater pool | Interior courtyard | Historic ice house, smokehouse, century-old grapevine, and stone walls | One hour from NYC | Asking $1,375,000
Listed by Todd Baker and Craig Smith of the Upstate Curious Team at Compass. For showings and inquiries, contact Todd at todd@upstatecurious.com, (917) 499-0901; or Craig at craig@upstatecurious.com, (845) 518-3844.
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