How To Spend A Long Weekend in Hudson Valley, New York

My husband and I just spent four full days exploring Hudson Valley, and it’s easily been one of the best trips we’ve ever had together. You can read all about the charming stone cottage we stayed in here, or continue reading to see our itinerary and dining recommendations!

I’m a big planner, while Matt prefers to go with the flow, so of course I planned the trip within an inch of its life and let Matt go with the flow that I’d painstakingly created. The activities we did and restaurants we visited are all about half an hour’s drive from each other, and we stayed in centrally located Saugerties to make accessing everywhere we wanted to go as convenient as possible. We could’ve easily filled a whole week with stuff to do, but that just means we’ll have to come back!

Getting There & Getting Around [if flying]

We flew into New York City, but it would’ve made a lot more sense to fly into Albany — I just didn’t realize that was an option until after we’d arrived! NYC is about a two-hour drive from where we stayed ,while Albany is just about 45 minutes.

Once there, you’ll need a car — opt for a rental that you’ll be comfortable spending some time in. You’ll likely want to explore multiple towns, and they’re all about 30-45 minutes from each other, which means a bit of car time each day.

Lodging

There are some great bed and breakfasts and hotels, but we chose to stay in a cottage rental that we’ve got a full tour of right here!

Activities

Horseback Riding in Catskill | This is a very beginner and kid-friendly hour-long excursion that brings you through gently sloping woods. Matt had never ridden a horse, so it was perfect for us, but if you’re an experienced rider you may want to opt for something more challenging! Nonetheless, we had an incredible time learning how to ride, looking out for mushrooms and taking in the views.

Mushroom Workshop at Sugarshack Mushroom Farm near New Paltz | Sugarshack is a small family-owned mushroom farm with an incredibly friendly and knowledgable team. They offer mushroom workshops and classes as well as farm tours! We did week three of their summer workshop series which was all about growing mushrooms in small spaces.

Fly Fishing in the Esopus Creek near Woodstock | We learned how to fly fish on a private guided tour through the beautiful Esopus Creek! Our guide, Doug, was a great teacher and very conscientious of us beginners.

Candle & Fragrance Making at Poured Candle Bar in Hudson | Enjoy a glass of wine while you peruse dozens of scents in the quest to make the perfect-for-you candle or fragrance! It was such a fun experience to do together and I highly recommend it.

Literary & Arts | The Hudson Valley is known for it’s history of being a literary and arts hub and there’s no shortage of things to do for anyone interested in a more cultured vacation! I loved this guide to the Hudson Valley’s Literary attractions (including dozens of adorable and unique book stores). Also do an events search on google for the dates you’ll be visiting! We did that and found a short film festival (by Throughline Artists) that became one of the highlights of our trip!

Dining

Our favorite breakfast / lunch: Hudson Roastery in Hudson. A gorgeous and quaint little cafe with shakshuka and lobster rolls and pastries and coffees and wines. A great place for breakfast, lunch or brunch.

Our favorite dinner: It’s a three-way toss up between the bistro-like atmosphere and extensive wine list of Red Onion (Woodstock), the most delicious Italian classics in the old school Annarella Ristorante (Saugerties), and the hip late night cocktails and bites at Huckleberry (New Paltz).

Our favorite cocktails: Early Terrible in Woodstock takes the win for being one of the coolest cocktail bars we’ve ever been to. It’s overgrown with fruiting grape vines and feels like a tree house but with a killer martini and original cocktails menu.

Featured