Rhinebeck is a charming, historic town nestled in New York’s scenic Hudson Valley. Located just east of the Hudson River, with its majestic views of the Catskill Mountains, Rhinebeck is easily accessible to New York City, the Berkshires, Connecticut and Upstate New York.

Tree-lined streets beckon with unique independent specialty shops offering apparel, home furnishings, books and gifts. The many fine and casual dining spots celebrate the Hudson Valley’s thriving locavore movement of boutique farms and orchards. Hotels, spas and B&Bs offer comfortable accommodations for rest and rejuvenation.

Rhinebeck is a cultural mecca boasting galleries, museums, performing arts, independent film, and historic homes and architecture. Hiking and biking trails provide outdoor enthusiasts places to explore the natural beauty of the region. Shops, galleries, restaurants, mansions, and friendly locals. The town’s two main streets intersect at Montgomery and Market Street, with plenty to do in each direction. To get here, you can take the Amtrak to Rhinebeck, take the bus to Kingston and cab over, or rent a car; it’s about a two hour trip either way.

Where to Stay in Rhinebeck, NY: Down on the Farm at Whistlewood Farm

whistlewood farm rhinebeck

We’re usually not big on bed & breakfasts, but WhistleWood Farm is too good to pass up. Located just three miles from town, this 7-room B&B was exceptionally cool. Eclectic antique furnishings, fireplaces, comfy sofas and chairs, warm handmade quilts adorn the place. Breakfast is large and delicious, with eggs fresh from the chickens that you’ll hear clucking away in the mornings. Every room is designed by Maggie, WhistleWood’s owner and caretaker for more than 30 years, who is delightful.

On the property, guests can take advantage of miles of hiking trails, and say “hi” to the friendly horses, cows, donkeys and chickens that live on the functioning farm. Being a farm-stay, you’d expect it to be crawling with kids and families–fortunately for us, it’s adults only.

Where to Eat & Drink in Rhinebeck, NY: Craft Beer Shop, Soul Food Restaurant in a Church, and Taverns Galore

rhinebeck grand cru

Rhinebeck has earned its name as a dining destination of Hudson Valley–you’d have to try pretty hard to go somewhere sub-par. That said, our first stop in the area is usually to Liberty, which is the hipster gastropub of the area. The cool thing about this place is the decor, with antiques covering every inch of the wall. They’re also a good bet for entertainment at night, booking shows in the bar area. For a snack or an awesome beer, we love Grand Cru Beer & Cheese Market. With 15 rotating tap lines and a walls worth of refrigerated beer, you’d be hard up to find something you didn’t like here. The snack and cheese menu are fantastic too.

For dinner, Terrapin is an interesting choice because of its location–in an old church. The dining room and bar have different menus here–we prefer the soul food menu and more laid-back atmosphere of the bar-side, aka the Bistro. If you’re in the mood for pizza (or just Italian), Market Street is absolutely fantastic. Ask to sit in the back room to watch the pizza guy in action. We’ve heard good things about Gigi Trattoria and The Local as well, but haven’t had the chance to try them yet.

rhinebeck foster tavern

For drinks only, we were lured into Foster’s Coach House Tavern because of the amazing sign. Packed full of equestrian stuff, it’s pretty divey but also really awesome. Outfitted with horse stalls that serve as dining booths, it’s half-creepy, half-cool. Much more inviting was the Tavern at Beekman Arms, which sits inside the oldest continually operating inn in America. The fireplace in the front makes this place extra cozy. Get all bubbly and stop by their antique market, which is fantastic.

What to Do Around Rhinebeck, NY: Hike to a Fire Tower, Take a Bike Ride, See an Indie Film

The town itself is really lovely, but there’s lots of opportunity to soak in the outdoors in and around Rhinebeck. One option is renting a mountain bike from Rhinebeck Bike Shop and pedaling over to Ferncliff Forest, a preserve two miles outside Rhinebeck with multiple bike trails. Ride until you reach the scenic observation tower, which offers spectacular views of the Hudson Valley and the Catskills. You can also drive to the trailhead and do this as a hike–it’s only a 25 minute walk to the tower.

The shopping in Rhinebeck is pretty decent as well, with lots of boutique shops and galleries worth popping into. Weirdly, we spent nearly an hour at Pure Mountain Olive Oil, which at first take I admit doesn’t sound that special. But being able to walk around and sample all the different olive oils I wanted was everything I never knew that I wanted. The staff was super friendly and didn’t mind us trying everything (and we did. try. everything.) There’s also a ton of antique shops, each with their own aesthetics and collections. Last, a sure-fire way to kill a rainy day here is by popping into Upstate Films. This nonprofit theater has shown the best indie, foreign and classic movies since the 1970s.