The Roxbury Motel’s theatrical exterior sets the stage long before you step inside. 📸 The Roxbury Motel
The Roxbury Motel • Address: 2258 County Hwy 41, Roxbury, NY 12474 • State: New York • Website: theroxburyexperience.com
Overview The Roxbury Motel is a Catskills landmark known for its theatrical design, storybook architecture, and commitment to doing things differently. From the exterior alone, it’s clear this is not a traditional roadside stay.
Why It’s Worth a Stop It’s memorable in the best way. The Roxbury leans fully into whimsy and creativity, making it a standout for travelers who appreciate humor, bold visuals, and a sense of play baked into their surroundings.
What to Know Before You Go • Every room is uniquely themed • Advance booking is strongly recommended • Located in the Catskills, about a scenic drive from NYC • Best suited for adults or older teens
Fun Fact Many guests return specifically to stay in a different themed room each time.
The Dogfish INN along the Lewes Canal, set inside a restored 1960s motel. 📸 Dogfish INN
Dogfish INN • Address: 105 Savannah Rd, Lewes, DE 19958 • State: Delaware • Website:https://www.dogfish.com/inn
Overview The Dogfish INN is a stylish, design-forward stay created by the team behind Dogfish Head Brewery. Set inside a restored 1960s motel along the Lewes Canal, the inn blends retro charm with modern touches, playful branding, and a relaxed, adventure-friendly vibe. It’s a welcoming spot for travelers who love good beer, good design, and easy access to town.
Why It’s Worth a Stop Guests get thoughtful amenities — growlers, outdoor fire pits, porch seating, and access to brewery experiences in Milton. It’s walkable to downtown Lewes, bike paths, and the ferry, making it one of Delaware’s most distinctive small-town stays.
What to Know Before You Go
Rooms are intentionally simple but stylish.
Fire pits and Adirondack chairs available for guest use.
Easy walk to Lewes shops, cafés, and canal front.
Bikes available seasonally.
Pet-friendly rooms available.
Fun Fact The inn’s library features beer-related books curated by the brewery team and City Lights Booksellers — a nod to founder Sam Calagione’s love of storytelling.
Overview Winvian Farm is an extraordinary 113-acre escape in the Litchfield Hills where luxury takes creative form. Guests stay in one of 18 themed cottages—each designed by a different architect—or in the historic Hadley Suite in the original 18th-century homestead. From the whimsical (a Treehouse or a Library) to the truly unexpected (a fully restored U.S. Coast Guard helicopter), no two stays are alike. Add to that a world-class spa, a celebrated farm-to-table restaurant, and a deep-rooted tradition of gracious hospitality, and you’ve got one of Connecticut’s most distinctive getaways.
Why It’s Worth a Stop Winvian Farm defies expectations with luxury that’s as playful as it is refined. It’s the kind of place you visit once and talk about forever. Whether you’re drawn to its architectural creativity, its serene countryside setting, or its warm, welcoming vibe, this is a stay that sticks with you.
What to Know Before You Go • Each cottage is completely different—be sure to browse the full collection before booking • The on-site restaurant is open to the public for dinner by reservation • Spa services book up quickly—reserve in advance • Guests must be 18+ unless visiting with a private group or for a full-property buyout
Fun Fact Winvian Farm was named for Winthrop and Vivian Smith, who purchased the property in 1948. Their daughter, Maggie Smith, transformed it into the imaginative retreat it is today.
Overview: Tarrywile Park & Mansion is a 722-acre preserve that includes rolling fields, dense woodlands, a peaceful pond, scenic picnic areas, and over 20 miles of hiking trails—all open daily to the public. At the center of the property is the Tarrywile Mansion, a striking Shingle Style home built in 1895. Once a summer estate, it now serves as a picturesque venue for weddings, reunions, and community events. With its historic charm and natural beauty, Tarrywile is a beloved part of Danbury’s landscape.
Why It’s Worth a Stop: Tarrywile combines nature, history, and community in one expansive setting. You can hike, fish, or picnic one day—and attend a formal event the next. It’s both a peaceful escape and a gathering place.
What to Know Before You Go: • Trails and grounds are open from dawn to dusk • Mansion visits are by appointment or reserved event only • Pets allowed on trails (on leash) • Park access is free, but donations are appreciated • The property is managed by a nonprofit trust and supported by the community
Fun Fact: The Tarrywile Mansion was once home to the Broughton family, who owned a hat factory in Danbury. Much of the home’s original stained glass and hand-carved details are still visible today.
Coastal charm, quiet mornings, and sunsets you’ll want to toast—Saybrook Point makes it easy to stay a little longer. 📸 Saybrook Point Resort & Marina
White Gate Farm • Address: 2 Bridge Street, Old Saybrook, CT • State: Connecticut • Website:https://www.saybrook.com/
Overview: Tucked where the Connecticut River meets Long Island Sound, Saybrook Point Resort & Marina blends seaside elegance with New England charm. This upscale resort offers thoughtfully appointed rooms, a waterfront marina, spa, wellness center, fine dining, and sweeping coastal views—whether you’re here for a quiet retreat or a special celebration. Guests can choose to stay in the main inn, the historic Three Stories guesthouse, or the romantic Lighthouse Suite perched right over the water.
Why It’s Worth a Stop: Saybrook Point delivers a full resort experience, from award-winning farm-to-table cuisine at Fresh Salt to the serene Sanno Spa. With indoor and outdoor pools, a marina with seasonal events, and close proximity to downtown Old Saybrook and scenic shoreline drives, it’s the kind of place that makes even a short stay feel like a true getaway.
What to Know Before You Go: • Offers a variety of accommodations, including waterfront suites and a stand-alone lighthouse suite • On-site amenities include full-service spa, fitness classes, marina, and fine dining • Walkable to the shops and galleries of Old Saybrook • Check the calendar for seasonal packages and special events • Ideal for romantic escapes, weddings, and wellness weekends
Fun Fact: The property sits near the site of the original Saybrook Colony, one of the earliest settlements in Connecticut, founded in 1635.
Evenings at White Gate Farm bring people together—lawn games, wood-fired pizza, and the kind of conversations that stretch past sunset. 📸 White Gate Farm
White Gate Farm • Address: 83 Upper Pattagansett Road, East Lyme, CT • State: Connecticut • Website:https://whitegatefarm.net/
Overview: Tucked into the countryside of East Lyme, White Gate Farm is a working organic farm with lodging options that blend comfort, history, and a deep connection to the land. Whether you’re staying in the 1765 farmhouse, the lakeside cabin, or a cozy guest suite, this is a place where food, nature, and community come together in simple, meaningful ways. Guests can wander the woods, paddle the lake, shop the weekend farm stand, or simply unwind by the pool.
Why It’s Worth a Stop: White Gate offers far more than a place to sleep. It’s a peaceful retreat where you can join a farm dinner, take a cooking class, help collect eggs, or stargaze through a telescope. The setting is serene, the accommodations are thoughtful, and the connection to Connecticut’s agricultural roots runs deep.
What to Know Before You Go: • The Inn at White Gate Farm has 7 bedrooms, 6.5 baths, a pool, and is available for private rental year-round. • Other options include the Innlet (2BR), and a rustic cabin right on the lake. • The farm stand is open Saturdays and Sundays, 9am–2pm. • Activities include kayaking, drumming circles, astronomy nights, and more (some require pre-booking). • Private catering, retreats, and small events welcome. • Farm-to-table meals and prepared foods are available by request or online.
Fun Fact: Built in 1765, the farmhouse once served as a “pest house” for smallpox patients in 1778. It was later home to silent film star Elsie Ferguson and eventually became the passion project of Ruth Lord, daughter of H.F. du Pont, who lovingly restored the land and passed it to her daughter, Pauline, the farm’s current steward.
