Thinking about taking a trip on your own? Do it. You don’t need a travel buddy to have an incredible getaway and Orange County, N.Y. makes it easy. Whether you’re craving some quiet time, want to explore somewhere new or just need a break from your routine, this is your chance to hit pause and reset on your own terms.
Only about an hour from NYC, Orange County offers a mix of walkable towns, scenic trails, cozy cafés and local experiences that are perfect for solo adventurers, especially if it’s your first time going it alone. You’ll find plenty to do, zero pressure to do it all and the freedom to make this trip completely yours.
This blog lays out two solo-travel paths, one curated with quiet moments, bookstores and wine stops in mind, and another that’s all about hitting the outdoors and sipping something strong. They’re tailored by vibe, not by rule, so take what you like and make it yours!
If your ideal trip includes a balance of self-care, vintage finds, great coffee and maybe a glass of wine at sunset, this one’s for you. Orange County offers just the right mix of calm and charm, perfect for solo travelers looking to unwind and rediscover their spark.
No solo getaway is complete without a bit of guilt-free shopping. Head straight to the iconic Woodbury Common Premium Outlets, home to over 250 high-end and designer stores like Kate Spade, Coach and Lululemon. With open-air walkways, mountain views and deep discounts, you can stroll, shop and splurge without a care in the world.
From there, ease into a slower, more intentional shopping experience with a thrifting trail through the county’s most beloved hidden gems.
● Newburgh Vintage Emporium is a treasure trove of antique home goods, vintage clothes and quirky finds that tell a story.
● Sugar Loaf Art & Craft Village is home to over 60 artists’ studios, galleries and shops set in 18th- and 19th-century barns.
● And at Jones Farm & Country Store in Cornwall, you’ll find fresh produce, homemade baked goods, local food, cafe meals to-go and gifts for every occasion.
Orange County’s coffee scene is as diverse as it is delicious. Whether you’re journaling, people-watching or just refueling between shops, you’ll love these solo-friendly spots:
● Valkyrie Coffee Roasters in Chester offers expertly brewed coffee with a modern, minimalist aesthetic that makes solo sipping feel stylish.
● Foundry42 in Port Jervis is part café, part boutique, and a great spot to grab a coffee and browse through something unique.
● Café Yen in Goshen is a peaceful hideaway with cozy vibes, great matcha and delicious baked goods that make solo afternoons feel like self-care.
For the reader-at-heart, nothing beats the serenity of solo bookstore browsing. Let your curiosity guide you through some of the coziest bookshops in the region:
● Blue Fox Books in Walden is a charming indie bookstore with hand-picked reads and the kind of quiet that makes you want to linger.
● Well Worn Books in Middletown specializes in used and rare books, perfect for wandering through old pages and new ideas.
● Montgomery Book Exchange has a hometown feel and a little bit of everything, ideal for finding your next read or a thoughtful souvenir.
Close your day with a glass of wine and a side of serenity. Orange County is home to some of the Hudson Valley’s finest wineries:
● City Winery Hudson Valley is a go-to destination set inside a restored industrial factory with river views, local wine and live music.
● Brotherhood Winery, the oldest winery in America, offers tastings, tours and a rustic, historic atmosphere that feels timeless.
● Christopher Jacobs Winery has a relaxed, country feel that’s great for slowing down and enjoying the view.
Solo travel isn’t just about quiet time, it’s also a great excuse to do what you love, explore what excites you and treat yourself to great food and craft drinks along the way. Orange County is packed with activities that hit the sweet spot between history, adventure and laid-back fun.
Start your day with a visit to one of Orange County’s U-Pick farms, where you can stroll the fields and fill your basket with fresh, local produce. It’s a hands-on, feel-good way to spend a solo morning and the perfect excuse to treat yourself to farm-fresh snacks.
● Soons Orchard in New Hampton is a family-run favorite known for its wide variety of U-Pick apples, fresh cider and homemade baked goods.
● Lawrence Farms Orchards in Newburgh is a popular U-Pick spot with seasonal fruits, scenic views and a relaxed, family-friendly vibe.
● Ochs Orchard in Warwick is a four-generation, family-run U‑Pick farm spanning over 150 acres and offers strawberries, cherries, raspberries, blueberries, peaches, apples, veggies, homemade ice cream, a petting zoo and a year-round market stocked with baked goods and local products,
If you love a good story, especially one steeped in American history, Orange County delivers:
● West Point Museum is a must-see, housing one of the largest collections of military artifacts in the country. It’s a powerful way to connect with the region’s past.
● At Washington’s Headquarters State Historic Site in Newburgh, you’ll walk the same grounds where George Washington made key decisions that shaped the nation.
● National Purple Heart Hall of Honor in New Windsor is a museum and registry dedicated to honoring Purple Heart recipients, from World War I to today, through interactive exhibits, a searchable Roll of Honor and stories of sacrifice and service
No solo trip is complete without some time in nature. Orange County is a paradise for hikers, paddlers and wanderers.
● Storm King Adventure Tours offers guided kayaking and paddleboarding excursions on the Hudson River, perfect for a little thrill and a lot of scenery.
● Drive the Shawangunk Mountains Scenic Byway and make stops along the way for hikes, photo ops or just taking it all in.
● Bear Mountain State Park rounds it out with hiking trails, picnic spots and an overlook that’s worth every step.
Reward yourself with a well-earned drink at one of Orange County’s top craft beverage spots:
● Orange County Distillery is a farm-to-bottle destination that’s perfect for a solo sipper looking to slow down with a strong cocktail.
● Drowned Lands Brewery in Warwick is a haven for craft beer lovers, earthy, experimental and wildly creative.
● Fox N Hare Brewing Co. in Port Jervis is friendly, fun and full of small-batch brews you won’t find anywhere else.
Solo travel isn’t just a getaway, it’s a chance to reconnect with yourself. In Orange County, N.Y., you’ll find everything you need for a meaningful escape. Whether you’re unwinding at a cozy bookstore, sipping wine at a quiet vineyard, hiking scenic trails or chasing your next adventure, the beauty of the Hudson Valley is ready to welcome you. Plan your perfect solo trip today at PickOCNY.com and let the journey begin.
Sleep in an architecturally significant B&B, or book a room at a nationally known hotel. Casual travelers as well as visitors looking for luxury will find a wide range of properties to consider. There are lodging options for everyone – Try our user-friendly lodging search below and come stay with us in Orange County, NY.
