NEWSLETTER
With crisp autumn air and stunning foliage views, fall in New York State is the perfect time to cozy up with the one you love on a romantic weekend escape. From chic Catskills retreats to a charming coastal bed-and breakfast on Long Island, root your stay in Black-owned accommodations for a getaway that combines comfort, connection, and culture. From scenic rail excursions to private wine tours to Black-owned dining spots, and deep dives into local Black history, choose a weekend itinerary that’s right for you and your boo. Photo Credit: Don Pollard/Office of Governor Kathy Hochul.
Explore this Article:
- Romantic Mountain Escape in the Catskills
- Lakeside Romance in the Adirondacks
- Wine Country Romance on Long Island's North Fork
- A Romantic and Culture-Filled Fall Weekend in Brooklyn
Romantic Mountain Escape in the Catskills
If you and your partner are craving crisp mountain air, colorful foliage, and uninterrupted time together, escape to the Catskills for a romantic fall getaway.
Where to Stay in the Catskills
Photo Credit: @abigaildoyle on Instagram
For your stay, choose between two Black-owned Catskills resorts, each offering a different kind of romantic escape. Settle into The Lorca Catskills, which offers private cottages and homes designed for slow mornings, evenings by the fire, and quiet time together in Shandaken. Nearby Urban Cowboy Lodge & Resort is nestled on 200 acres set along Esopus Creek with signature soaking-tub suites, an Estonian sauna, and fun amenities such as tennis and bowling that provide couples a romantic place to unwind after a day in the mountains.
After checking in, ease into the getaway with a relaxing evening. At Urban Cowboy, settle in by the fire, enjoy dinner on-site at The Dining Room, and take in the peaceful mountain setting before the next day's adventures. If you are staying at The Lorca, pick up a take-out dinner from Peekamoose Restaurant and enjoy a cozy meal indoors or bring your own ingredients to cook dinner together in your fully-equipped kitchen.
Day One: Laid-Back Rail Excursion and Catskills Mountain Adventure
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Begin your first full day with breakfast or brunch at Phoenicia Diner, a Catskills favorite serving dishes made with regional ingredients. Afterward, explore Phoenicia, where independent shops and a relaxed mountain-town atmosphere offer an easygoing start to the day.
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From there, shape the rest of the day around the kind of experience you want to share. For a relaxed outing, head to Rail Explorers: Catskills and pedal side by side along historic railroad tracks surrounded by colorful mountain scenery. Then, stop at the nearby Empire State Railway Museum to learn how rail travel helped shape tourism throughout the region (open 10am-4pm, Saturdays, Sundays and holidays from Memorial Day through Columbus Day).
Couples craving more time in the mountains can instead make an outdoor adventure the highlight of the day. For a shorter, moderately challenging hike, begin on the Phoenicia–East Branch Trail, and continue toward Giant Ledge to experience breathtaking mountain scenery. The approximately 2.7-mile round-trip hike leads to several overlooks with sweeping views of the surrounding mountains and vibrant fall foliage.
For a more demanding mountain climb, explore Slide Mountain Wilderness and take the approximately 5.4-mile round-trip hike to the top of Slide Mountain, the tallest peak in the Catskills. Couples looking for a more relaxing way to enjoy the mountain scenery can instead visit Belleayre Mountain for a scenic gondola ride above the changing landscape. During the fall, scenic gondola rides are offered through October 11, 2026, on Saturdays and Sundays from 10:00 a.m. to 5:00 p.m.
Day Two: Scenic Catskills Drives and Local Sips
The following day, take a drive along the Catskill Mountains Scenic Byway to Hunter Mountain, where the surrounding mountains are covered in red, orange, and gold foliage. Ride the Scenic SkyRide for panoramic views and explore the seasonal activities taking place at the resort. On select October weekends, Colors in the Catskills adds live entertainment, local vendors, specialty food and drinks, and more ways to enjoy the season together.
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Complete the outing at Hunter Mountain Brewery, a casual American-style brewpub with more than 15 taps featuring its own craft beers and selections from other New York breweries. Sample a flight of craft beers alongside burgers, wraps, and other pub favorites, and enjoy the relaxed atmosphere together.
Lakeside Romance in the Adirondacks
For a fall getaway shaped by peaceful lakes, scenic drives, and outdoor adventure, head to the Adirondacks.
Where to Stay in the Adirondacks
Make The Lorca Adirondacks, a Black-owned lodging property in the town of Indian Lake, your home base for a fall escape centered on scenic drives, outdoor adventures, and quiet evenings beneath the trees. Surrounded by Adirondack woodlands and located near Indian Lake, The Lorca offers couples a comfortable place to slow down and enjoy the season, while also serving as a convenient base for exploring nearby towns, lakes, and trails. The balance of rest and exploration is what makes the stay feel complete.
After checking in, keep the first evening simple. Explore the grounds, take a short drive into Indian Lake for a movie date or live performance, or enjoy a casual meal outdoors before returning to the property. As the sun sets and the air cools, settle in beside the fire and ease into the rhythm of the mountains. It's a quiet, grounding start that sets the tone for a getaway shaped by connection, nature, and the beauty of the Adirondacks.
Day One: Take the Scenic Route to Blue Mountain Lake
The next morning, follow Route 28/30 from Indian Lake toward Blue Mountain Lake. The approximately 20- to 25-minute drive passes through mountain scenery and fall foliage, making the journey between destinations part of the getaway.
Begin with breakfast or an early lunch at Chef Darrell's Mountain Diner, a Black-owned local favorite located directly along the scenic route. Housed in a restored 1950s diner car, it is an easy and natural stop on the way to Blue Mountain Lake, serving hearty, home-style dishes in a relaxed setting.
From there, continue toward Blue Mountain Lake to visit Adirondack Experience, the Museum on Blue Mountain Lake. Explore exhibits focused on the region's history, art, culture, and relationship with the natural environment while moving between indoor galleries and the museum's scenic outdoor grounds. Their on-site cafe offers a convenient and scenic place to grab a bite to eat while taking in spectacular lake views from their outdoor deck.
Day Two - Paddle and Hike on Indian Lake
The next day, set out for a full day of nature and adventure on Indian Lake. Bring water, a few snacks, sunscreen, insect repellent, and a light waterproof layer. Wear comfortable clothing and sturdy hiking shoes, and use a dry bag to protect your phone, keys, and other small belongings while you are on the water.
Head to Indian Lake Marina to rent a canoe, paddleboard, kayak, or boat and prepare for an adventure across the lake. Rentals are available through October 12, making this experience best suited for an early-fall getaway. After getting fitted with the necessary equipment, paddle approximately 30 minutes to the Baldface Mountain trailhead, accessible only by water, taking in views of the wooded shoreline, small islands, and fall foliage reflected across the water along the way.
Once you reach the opposite shoreline, secure your vessel and begin the approximately 1.7-mile hike through Baldface Mountain trail. The moderate forest hike leads to an open overlook with views of Indian Lake, Snowy Mountain, and the surrounding Adirondack landscape. At the top, pause to enjoy your snacks while taking in the sweeping fall scenery, snapping photographs, and resting before following the same trail back to the shoreline.
Paddle back across Indian Lake, return your rental, and head to Indian Lake Restaurant & Tavern for dinner. The casual local restaurant offers American comfort food, a full bar, and a selection of local and seasonal beers, making it an easy place to unwind after an active day.
End the evening back at The Lorca, where you can relax by the fire and enjoy the quiet surroundings after a day spent on the lake and mountain.
Wine Country Romance on Long Island's North Fork
For couples drawn to vineyard roads, coastal views, and crisp fall afternoons, Long Island's North Fork offers a romantic escape rooted in wine country charm and coastal calm. Bonus: With Black-owned lodging, a Black-owned private winery tour company, Black-owned dining, and a meaningful Black cultural experience woven into the itinerary, couples can discover Long Island through a getaway that feels romantic, personal, and thoughtfully planned.
Where to Stay in the North Fork
Make Arbor View House Bed and Breakfast, a Black-owned inn in East Marion, the center of an intimate getaway filled with wine, seasonal flavors, waterfront scenery, and time to reconnect.
Set inside a historic home, Arbor View House offers individually designed guest rooms, gourmet breakfasts, spa services, and personalized hospitality. Its location places couples near vineyards, beaches, and the waterfront communities of Greenport and Orient, making it easy to explore the North Fork while returning each evening to the comfort of the inn.
After checking in, take time to settle into the slower rhythm of the area. Unpack, explore the property, and relax before heading to The Halyard Restaurant for dinner. Set along Long Island Sound, its seafood-focused menu and waterfront views create a romantic introduction to the North Fork. Time your reservation around sunset and watch the changing light over the water as you enjoy your first evening together.
Day One: Travel Through Wine Country With a Private Guide
Credit: Courtesy of Sannino Vineyard Bed & Breakfast
The next morning, have a gourmet breakfast at Arbor View House before setting out on a private wine-country experience designed especially for two. Through North Fork Taste and Tours, a Black-owned company founded by Arbor View House innkeeper Wilfred Joseph, you and your boo can leave the route planning and driving behind to focus entirely on enjoying the day together on your private wine-country journey.
Credit: @liwinecountry on Instagram
Settle in beside each other as your guide leads you along quiet country roads lined with farms, vineyards, and fall scenery. Because the tour company curates the itinerary, each winery will feel like a unique discovery. Spend the day tasting new wines, comparing your favorites, and taking photographs together to remember the journey.
Photo Courtesy of NYS Parks
As an alternative to the day’s adventure, you can opt to have bicycles from Dan's Bike Rental delivered directly to Arbor View House for $35/bike/day. Set out for a leisurely ride east toward Orient on country roads surrounded by farmland, coastal scenery, and changing fall colors. Spend time exploring the quiet streets of Orient Village or continue toward Orient Beach State Park for views of the water and the surrounding maritime landscape.
Day Two: Explore African American History on the East End
Take time to rest and freshen up before driving to Greenport. From there, drive your car aboard the North Ferry for the short crossing to Shelter Island. Continue across Shelter Island and take the South Ferry to North Haven before driving into Sag Harbor. Both ferries generally depart every 8 to 15 minutes, operate on a first-come, first-served basis, and accept cash only, so travelers should allow extra time for boarding. The two waterfront crossings add a scenic element to the journey and make traveling between the North and South Forks part of the day’s experience.
Visit the Eastville Community Historical Society, where the Heritage House and St. David AME Zion Church preserve the stories of African American, Indigenous people, European immigrants, and working-class families who helped shape the historic Eastville community. Learn about the Black residents who contributed to the area’s development and the church believed to have been connected to the Underground Railroad. Arrange the visit in advance, as tours and exhibits are available by appointment only.
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Afterward, explore Sag Harbor’s historic streets and waterfront before beginning the return journey, making a stop for dinner on Shelter Island at Commander Cody’s Seafood Market & Restaurant, a local Black-owned gem offering fresh seafood, barbecue, and a relaxed island atmosphere. Because the restaurant closes at 8PM, travelers should plan to leave Sag Harbor by 5PM and arrive at the restaurant by 6PM, allowing enough time to order and enjoy dinner without feeling rushed.
After dinner, continue north across Shelter Island and take the North Ferry back to Greenport before ending the evening at Arbor View House. During the fall, the final North Ferry departs Shelter Island at 11:45 p.m., leaving ample time to return after dinner.
Day Three: Slow Down and Savor the North Fork
After several days of exploring, leave time to enjoy Arbor View House itself. Sleep in, enjoy breakfast together and schedule a spa service before spending a relaxed afternoon together at the inn.
That evening, head to North Fork Table & Inn in Southold. Set inside a historic countryside home, the restaurant serves a seasonal menu inspired by Long Island’s farms, vineyards, and surrounding waters. Enjoy an intimate dinner that reflects the flavors of the region before returning to Arbor View House for a quiet final evening together.
A Romantic and Culture-Filled Fall Weekend in Brooklyn
For couples looking to pair romance with art, Black history, and memorable dining, Brooklyn offers a fall getaway filled with brownstone-lined streets, neighborhood culture, and lively evenings.
Where to Stay in Brooklyn
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Make Akwaaba Mansion, a Black-owned bed-and-breakfast in historic Bedford-Stuyvesant, your home base for an intimate fall escape in Brooklyn. Set inside an elegant 1860s Italianate villa, Akwaaba Mansion blends historic architecture, antiques, Afrocentric design, Southern-style breakfasts, and personalized hospitality. Its sun porch, secluded garden, individually-designed rooms, and available wellness services give couples several ways to slow down together between outings.
After settling in, take time to admire the beauty of the mansion before heading out for a leisurely walk through Bed-Stuy, passing rows of historic brownstones, tree-lined blocks, neighborhood murals, and locally-owned businesses.
With check-in at 2pm, that leaves you time to pop into the Richard Beavers Gallery, a Black-owned contemporary art gallery to admire works by emerging and established Black artists, or grab a signature biscuit sandwich at Brown Butter Craft Bar & Kitchen, a Black-owned neighborhood favorite located along the stretch of Tompkins Avenue known as “Black Girl Magic Street” for its high concentration of businesses owned by Black women.
Day One: Explore Brooklyn's Black History and Fall Scenery
The next morning, enjoy a Southern-style breakfast at Akwaaba Mansion—think fluffy biscuits, grits, eggs, and seasonal specialties—before heading to Weeksville Heritage Center in Crown Heights. The site preserves the history of Weeksville, one of the country's earliest free Black communities, established by Black landowners before the Civil War.
Tour the historic Hunterfly Road Houses and learn how Weeksville residents created homes, schools, churches, businesses, and civic institutions within a thriving independent community. The preserved houses and stories of the people who lived there offer a deeper understanding of Black life and self-determination in 19th-century Brooklyn.
Credit: @joeribsnyc on Instagram
After the tour, continue to nearby Prospect Park for a slower afternoon beneath the changing leaves. Follow the wooded paths, walk beside the lake, and find a quiet place to sit together while enjoying the crisp fall air.
Return to Akwaaba Mansion afterward to rest and get ready for dinner at Kokomo in Williamsburg. The Black-owned restaurant combines Caribbean-inspired cuisine, cocktails, music, and a lively atmosphere, turning dinner into part of the evening's entertainment. Share a few dishes, enjoy the energy of the dining room, and end the night with a taste of Brooklyn's contemporary Caribbean culture.
Day Two: Follow Black Stories from Brooklyn to Lower Manhattan
Ease into the next day with brunch at Peaches, a Black-owned neighborhood favorite within walking distance of Akwaaba Mansion. Settle in with Southern-inspired comfort food before making your way to Brooklyn Heights for a day that pairs waterfront scenery with Black history in Lower Manhattan.
Photo by Julienne Schaer
Once in Brooklyn Heights, head to Brooklyn Bridge Park for a romantic walk along the East River. Take in views of the Brooklyn Bridge and Lower Manhattan skyline, stop for photographs along the promenade, and enjoy the contrast between the waterfront scenery and the surrounding city.
Before leaving the neighborhood, stop at Cloudy Donut Co., a Black-owned bakery known for small-batch vegan doughnuts in creative, rotating flavors. Choose a couple of doughnuts to share while enjoying a quiet break near the waterfront.
From there, cross into Lower Manhattan for a Black Gotham Experience walking tour at the South Street Seaport. Through storytelling, visual art, and immersive interpretation, the Black-owned cultural organization highlights the impact of the African Diaspora in early America. The experience offers a meaningful way to see familiar streets through stories that are often left out of traditional accounts of the city's history.
End the day with a special-occasion dinner at the 2-Michelin-starred SAGA, set high above Lower Manhattan. Led by acclaimed African American Executive Chef Charlie Mitchell, the tasting menu experience draws from personal memories, Southern influences, and contemporary fine dining. Pair the meal with sweeping skyline views for an elevated final night of the getaway.
Discover more inspiration through I LOVE NY Black Travel blogs, seasonal guides, and curated experiences—and be sure to tag your travels on Facebook, X, Instagram, and TikTok using #ILoveNY and #iSpyNY.