Dreaming of a cozy escape to unwind, reconnect, and indulge in some of the best food, drink, and scenic views New York has to offer? A Hudson Valley getaway is the perfect solution. This three-day itinerary has everything you need for a late-winter retreat bursting with romance, relaxation, and discovery. Here’s your perfect weekend guide through the spectacular Hudson Valley.
Day 1
Start with the Iconic Moodna Viaduct
Kick off your weekend getaway with a visit to the stunning Moodna Viaduct. This historic railway trestle is a great way to discover our region’s enchanting beauty. The views here will take your breath away and make for some fantastic Instagram-worthy shots!
Lunch at Bella Luna Restaurant & PizzEria
Bella Luna Restaurant & Pizzeria is a local gem in the heart of Salisbury Mills. Treat yourself to a hearty wood-fired pizza or one of its signature pasta dishes. Its laid-back atmosphere is the perfect warm-up to your Hudson Valley adventure.
Wine Tasting at Brotherhood Winery
Swing by Brotherhood Winery in Washingtonville for a cozy afternoon of wine tasting. America’s oldest winery dates back to 1839. Sip on crafted reds, whites, or sparkling wines. Enjoy one of its beautiful cellar tours. Brotherhood Winery is the perfect spot for anyone looking for a date night idea, great wine, and history!
Dinner at 1839 Restaurant and Bar
Your first day ends with a culinary bang at 1839 Restaurant and Bar. This place is minutes from Caldwell House Bed and Breakfast. 1839 is one of the best restaurants in the Hudson Valley for an intimate dinner. And it’s known for its locally-inspired dishes and crafted cocktails. Don’t forget to order their famous braised short ribs!
Day 2
Shop or Create at Hudson Beach Glass
Embrace your inner Michaelangelo with a visit to Hudson Beach Glass in Beacon. Then get ready for a fun and unique time learning about glass-blown art.
You could browse their stunning collection of handmade glass art. However, a more interactive option is to sign up for a workshop. You’ll create a sparkling masterpiece to take home. This unique experience captures the charm of Hudson Valley’s artisan culture. And it’s a lot of fun!
Lunch at IL’ Cenacolo Restaurant
Foodies, rejoice, and let your taste buds do the happy dance! For lunch, visit IL’ Cenacolo Restaurant. This must-visit hidden culinary gem is in Newburgh, close to our last stop.
You’ll step into a warm, welcoming atmosphere. This restaurant is perfect for any foodie — new or well-seasoned. We love that IL’ Cenacolo creates authentic Italian dishes with fresh, locally sourced ingredients. So, each mouth-watering bite is bursting with flavor.
Explore the DIA: Beacon
Art lovers won’t want to miss DIA: Beacon. This place hosts massive contemporary installations and mesmerizing artworks. The huge museum has made its home in a former printing factory. So, it’s the ideal place to wander and reflect, especially during winter.
Dinner with a View at Blu Pointe
A Hudson Valley classic, Blu Pointe in Newburgh is the ultimate dinner destination. Located along the Hudson River, this guest-favorite features elevated seafood dishes and stunning river views. Try their signature lobster mac and cheese or the raw bar for something extra special.
Day 3
Start with a Couples Massage at Caldwell House Bed and Breakfast
Why not start your final day with some relaxation? After all, you deserve it! Treat yourself and your partner to a rejuvenating couples massage in the massage room at our Connemara House. You’ll finish feeling refreshed and ready to tackle the rest of your adventure.
Trot Through Trestle Valley Equestrian
Head over to Trestle Valley Equestrian. That’s right, it’s time to get on your horse and ride. But seriously, there are few better things to do in the Hudson Valley than exploring nature’s beauty on horseback.
Trestle Valley has professional guides and well-trained horses to get you started on the right foot — or hoof. A horseback ride is one of the best ways to experience the peaceful winter landscape in a uniquely memorable way.
Lunch at Loughran’s Irish Pub
Ready for a hearty lunch? If you’re nodding your head, then it’s time to warm up at Loughran’s. We may be a little biased (Caldwell House is steeped in Irish history), but this cozy Irish pub hits the spot. It serves up hearty comfort food like Irish bangers and mash, alongside phenomenal beer like Guinness.
Hike at Hudson Highlands Nature Center
Ready to head outdoors again? Bundle up, and head to the Hudson Highlands Nature Center for a short winter hike!
One of the great things about this place is its well-marked trails. They’re beginner-friendly and offer gorgeous views of the frosted hills and valleys. So, bring your camera or smartphone to snap a pic and make those co-workers back at the office jealous.
End with Dinner at Canterbury Brook Inn
Close out your weekend with a romantic dinner at the Canterbury Brook Inn in Cornwall. Their Swiss-inspired hospitality and menu selections, including grilled bratwurst and schnitzels, are the perfect way to cap off your Hudson Valley getaway on a high note.
Plan Your Hudson Valley Getaway Today!
The Hudson Valley is calling, and this cozy late-winter escape awaits your arrival! So pack your bags and get ready for this Hudson Valley getaway! This three-day itinerary has everything needed to reignite your wanderlust. With Caldwell House as your home base, you’ll have plenty of luxurious relaxation and time to recharge each evening.
Don’t wait to book your room, though. These winter weekends fill up fast. Reserve your stay at Caldwell House today.
Photo Credit: © AleksandarNakic from Getty Images Signature via canva.com, © gilaxia from Getty Images Signature via canva.com, © Rocket k from Getty Images via canva.com, © Samuel Borges Photography via canva.com
