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The Village of Rhinebeck, NY - A Quaint New York Getaway

The Village of Rhinebeck, NY - A Quaint New York Getaway

I squinted my eyes and looked closer at my phone. According to my GPS, I was about five minutes from my intended destination of Rhinebeck, New York, and yet, as far as I could see, I was in the middle of a forest.

And then, like a welcomed mirage, signs of an upcoming village began to take shape. A stately house on my left, a manicured garden on my right, and then, finally, the village of Rhinebeck straight ahead.

I quickly decided that if I ever decided to drop the blog, give up the social media, and go off the grid, Rhinebeck would be an awfully nice place to take a breather. In Rhinebeck, people walk up and down the street with a knowing smile, as if everyone is in on a shared secret. That aforementioned secret, of course, is one I’m sharing with this very article - the village of Rhinebeck, in Dutchess County, is quietly one of New York State’s top weekend getaways. Heck, if your schedule allows it, it’s one of the top weekday getaways as well.

Where is Rhinebeck, New York, Anyhow?


Well, for starters, I’m guessing all of us have pieced together that I’m talking about a town in New York State.

For reference, in this post, I’m primarily referring to the “village of Rhinebeck,” or Rhinebeck proper, as opposed to the town of Rhinebeck. From a census perspective, the “town of Rhinebeck” actually includes surrounding communities such as Rhinecliff, Württemberg and so forth. The village of Rhinebeck has around three thousand people, while the town has closer to ten. We’re not talking about big numbers either way, but I strive to show I care enough to do my research, so I wanted to make that distinction.

Rhinebeck, NY is located firmly in Dutchess County, a historic county established in 1683 that is a tourism hub for the state because of its plethora of historic sites, towns and cities worth visiting, and nature galore. It is located in the Hudson Valley in what people would identity as the “Mid-Hudson Region.”

Rhinebeck is a roughly two hour drive from New York City, which quickly puts it into the category of appealing weekend trips from NYC. New York City, as we all know, comes with a certain amount of chaos, and you could put forth the argument that Rhinebeck is an ideal antidote to said chaos. I wasn’t there with my wife, Bri, but it did also strike me as somewhere you could talk about as a romantic getaway near NYC as well.

Many people that I had the chance to interact with mentioned the ease of taking the 1 hour and 40 minute train ride from Penn station to Rhinecliff (a short drive away from Rhinebeck). With that service, it’s awfully easy to imagine leaving after work on Friday, and exchanging horns and bright lights, for a soft breeze and the pleasant hum of the main street of an historic village.

I actually drove from Toronto, and didn’t find it all that bad. It took me about seven hours, but as a younger man than I am now, I took road trips that were a lot longer and more arduous than that. I actually love driving and listening to podcasts, and just being “off the clock.” If you want some podcast recommendations, by the way, be sure to subscribe to my newsletter. You can also check out my podcast, Rick Steves Over Brunch.

Why Rhinebeck?

The Beekman Arms - Delameter Inn is one of the most iconic buildings in Rhinebeck, NY, a great New York getaway

I’m a sucker for history, so I was immediately enamoured with the notion that a European settlement was formed in this area all the way back in the late 1600’s. It was officially incorporated in 1834, but the village and the area around (and Dutchess County at large for that matter) is dripping with history, and I’ll get to some of that when I’m mentioning which historic sites you may want to visit in and around Rhinebeck down below.

Even if you aren’t a history buff, Rhinebeck is pretty darn adorable. The main throughway in Rhinebeck is Montgomery Street, which is then called Mill Street south of Market Street. Just wander a bit when you’re there - stroll down Chestnut, get a feel for both East Market and West Market Street, go all the way down to Legion Park if you feel like it. It’s a good place to get lost, largely because you’ll never be too lost.

The centre of town is filled with local restaurants, bars, cafes, hotels and inns which appropriately reflect the ethos of the town. That being said, it’s also important to get outside of town. I had no idea before arriving all that I could see within a fifteen or twenty minute drive of Rhinebook. That’s why, when I’m talking about things to do in Rhinebeck, NY in this post, I will ultimately try to talk about what to do in the village and town proper, but also what’s nearby that you might not know about. In fact, those will be two separate sections for the sake of ease.

Rhinebeck, NY Restaurants of Note

Considering the size of Rhinebeck, I was rather impressed with the array of restaurants on offer. Thankfully, as you may know if you’ve been following my blog or brand for a while, I’ve got quite an appetite, so I was able to do a good number on the Rhinebeck restaurant scene. You know, I’m all about gathering that information for you guys, right? It has nothing to do with my propensity for overeating, I swear.

Let’s talk about a few Rhinebeck restaurants that you should consider popping into if you find yourself in this lovely little part of New York State.

Terrapin Restaurant

Terrapin restaurant may just be the best of the best in terms of Rhinebeck restaurants

Terrapin isn’t just a celebrated restaurant in Rhinebeck, it’s regularly in discussion for one of the top restaurants in the Hudson Valley. They focus on a farm-to-table mentality that highlights the Hudson Valley, but look beyond the Hudson Valley in their attempt to put a spin dishes from around the world. While there, I tried the morel and wild mushroom bisque, spinach and artichoke dip with goat cheese, truffled fig, brie and roasted shallot quesadilla, and followed all that up with the braised short rib gratinée.

The answer is yes, I was quite full, but also yes, it was worth it. I was lucky enough to dine with Whitney and Dawn from Dutchess County Tourism, and that just made the meal all the more enjoyable, as they’re both wonderful, warm people. Patrick was our attentive and eccentric server who did a brilliant job looking after us. I recall when I asked if the dessert was local as well, he give me a look and said, “No Chris, it was made by nuns in the Poconos!” All joking aside, I’m almost intolerably indecisive when it comes to choosing food (My wife, Bri, will attest to that), so it was helpful to have a decisive server like Patrick who knew the menu like the back of his hand. Heads up, you’ll likely need reservations.

Bubby’s Take Away Restaurant

Bubbby’s Take Away Kitchen was one of the top Rhineback restaurants in Rhinebeck, NY

I should note that this restaurant is technically in nearby Red Hook, but it’s just a short ten minute drive away from Rhinebeck.

Anyway, this is the ideal spot to come if you’re somebody who likes to enjoy a hearty, healthy lunch that won’t leave your stomach grumbling for dinner in the late afternoon.

I’d describe it as “Mexican-ish,” as they dapple in tacos, quesadillas, burritos and so forth, but they also try their hand at things such as Caribbean chicken an veggie dishes. It’s a spot that is bright and colourful inside with plenty of natural light to bask in while enjoying your meal. I personally had a dish that I haven’t been able to get out of mind since I tried it, and that’s the “Cauliflower Coconut Curry.” It is as it sounds, with plenty of cilantro, cashews, and all that on a bed of coco rice. Honestly, even I go back to do another roundup of Rhinebeck, NY restaurants, I’ll still go out of my way to get this dish.

Market St.

Market St. in Rhinebeck, NY is one of those Rhinebeck restaurants to keep an eye on!

I’m a fan of asparagus, so I was only too happy to dive into the wood oven roasted asparagus with truffle mushrooms and spicy yogurt, but the rare beef pizza (which was on special that night and pictured above) was also quite delicious. With Market St., you’re getting a reliable place in the centre of Rhinebeck with a hip, pleasant ambiance and good service. They do a fair amount of experimentation with their drinks and desserts as well, so if that’s your thing, this might be a place to look out for.

Other Rhinebeck Restaurants to Consider:

I’ll list a few more restaurants below which you might want to visit while you’re there. Remember, Rhinebeck has shifted from a place that people visit for a few hours to a place that people are now staying for a few days, so I feel it’s worth noting a few more restaurant recommendations for those looking to really get to know the Rhinebeck food scene.

Thankfully, whatever your choose, you won’t be walking far. It’s hard to imagine until you get there how many quality restaurants are packed into the village of Rhinebeck!

  • Pizzeria Posto - People rave about their Neopolitan style pizzas made in a calm, cozy setting that anyone can get on board with.

  • Cinnamon Indian Cuisine - Right next door to Pizzeria Posto, you’ll find Cinnamon Indian Cuisine, a restaurant bringing high-quality Indian and Sri Lankan fare to the village of Rhinebeck.

  • Le Petit Bistro - It’s a little pricey, but good French cuisine doesn’t come cheap. It’s busy, so make sure if you reservations if you want to ensure that you can get your hands on their famous duck, escargot, and other French delights.

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Things to do in the Adorable Village of Rhinebeck, NY

There’s not too much ground to cover, but it’s certainly worth the venture to pop in and out of a few places. In fact, within the village of Rhinebeck itself, I’d say that’s what it’s all about.

Pop in to Samuel’s Sweet Shop

Samuel’s Sweet Shop in Rhinebeck, NY has that classic candy store feel to it. It’s one of the top things to do in Rhinebeck.

Samuel’s almost closed in 2014, but when it appeared it might, a slew of celebrities teamed together to save this little candy shop, including the likes of Paul Rudd. It’s one of those candy stores that is tiny as can be, but filled to the brim with delights. I recently read an interview with Paul Rudd where he talked about loving owning a candy store because it’s impossible to walk in and not be in a good mood, and I think that’s about right. The store fits in perfectly in Rhinebeck, so it’s great that it was saved and can continue to be included on places such as my, “things to do in Rhinebeck” list.

Recall the Joys of a Local Bookstore at Oblong Books & Music

Oblong Books & Music in Rhinebeck, NY is part of what makes Rhinebeck one of the top New York getaways!

I love this place, I just love it, and I’ll tell you why.

For one, I was an English major in school, so I believe in the power of the book to transform lives, but what I loved about this bookstore in particular was how personal it was. Throughout the store, there are little cue cards attached just below certain books which talk about why the book may or may not be suited for you. I’ve never seen that before, and I was blown away by that. There must be a hundred different cue cards throughout the store that guide you on a literary adventure of sorts.

Did I mention I loved it?

Get Your Stationary Fix at Paper Trail

Paper Trail in Rhinebeck, NY is a great stationary store and part of what makes Rhinebeck of the great New York getaways!

I’m such a sucker when it comes to this stuff. Notebooks imported from Japan? Pens and pencils from Scandinavia? The soft scent of lavender candles somehow permeating the store? Where do I sign?

Really though, this is the sort of spot I could spend far too long perusing and not get bored. It’s a little pricey, yes, but they’ve got a pretty neat collection of paper, jewellery, gifts, books, and everything in between.

Get a Little Lost in the Streets of Rhinebeck

The village of Rhinebeck in New York is adorable!

Yes, I mean it. It’s not big, so the stakes are pretty low. The truth is, I can try to guide you, but there are going to be things to do in Rhinebeck that are perfectly suited for you that I might have missed - it’s that sort of place. If you do a little wandering around the village of Rhinebeck, NY and do find a neat store or place to walk into, do let me know and I can add it to my list. Feel free to shoot an email along to chris@travelingmitch.com, or just comment below.

Really though, it’s today’s society we spend a lot of time with all aspects of our lives heavily scheduled. I’d encourage you to set aside a couple of hours to let you find your Rhinebeck. Obviously, I want this article to be as helpful as possible in guiding you, but ultimately you’re the master of your own ship, and that’s a beautiful responsibility in and of itself.

Things to do Near Rhinebeck, NY

You could argue that what’s around Rhinebeck is even more exciting than what you’ll find in Rhinebeck proper, so let’s talk about that, shall we? What can you do within let’s say a twenty or so minute drive of the centre of Rhinebeck (or less)?

The Old Rhinebeck Aerodrome

The Old Rhinebeck Aerodrome is an institution in the Dutchess County area! It’s one of the top things to do in Rhinebeck!

As someone who flies a lot and is interested in flight, a visit to the Old Rhinebeck Aerodrome was certainly on my list of things to do near Rhinebeck. I was lucky enough to get a tour with the likes of Stew Sommerville, a man whose passion for flight is nearly unparalleled. He’s the sort of guy that can’t help using the pronoun “she” when talking about old airplanes.

He walked myself and Whitney through the old hangers, and it’s clear that they’ve got some impressive old planes, many of which they still fly in their airshows. I remember before we were leaving I saw this gorgeous old plane sitting in the hanger and a pilot heading towards the hanger. I asked Stew if that old plane could still fly and he smiled and said, “ Oh the Curtiss JN-4? Yup! She’s a crotchety old bird, but that’s understandable seeing as she’s 102 years old and all.”

Visit a Nearby Historic Site

You may have envisioned your New York getaway being all about rest and relaxation, but make no mistake - there’s plenty of learning to be done and history worth noting around this area.

Wilderstein Historic Site

The Wilderstein Historic Site might just be the most impressive site in the Rhinebeck area, and one of the top things to do in Rhinebeck to be sure.

Wilderstein, in my opinion, is the historic site that you should visit above all others. Firstly, it’s likely the most prominent example of Victorian architecture in the Hudson Valley. However, perhaps even more interestingly, it was also the home of Margaret Suckley, a cousin and very close friend of Franklin Roosevelt. I would recommend booking a tour to get a full feeling for the property. Joe was my guide, and he did an excellent job, so don’t hesitate to book with him!

Wilderstein Historic Site has over 200 volunteers, so the buy-in on this place in the Hudson Valley region is just enormous, and rightfully so. I’d never seen anything like it, and the views of the Hudson River are certainly nothing to scoff at.

They run tours at Wilderstein from May through October.

Clermont State Historic Site

The Clermont State Historic Site is not far at all from Rhinebeck, NY, which makes it an easy drive through Dutchess County.

I appreciated getting to see the Clermont Estate largely as I’m a history buff, so it was fascinating for me to see the former estate of the Livingston family. The Livingston family had members of the family sign the Constitution, the Declaration of Independence, and its descendants include the likes of the Bush family, and First Lade Eleanor Roosevelt.

The property was designated a New York State Historic Site and United States National Historical Landmark in 1972, so it’s got some clout, but for history lovers, both the Clermont and Wilderstein Estates will have a certain appeal.

They run tours at Clermont State Historic Site from April through October.

Dayton Grant Park at Burger Hill

Dayton Grant Park at Burger Hill is a can’t miss spot if you’re on a New York getaway to Rhinebeck

If you don’t mind a small walk to get a panoramic view from the Berkshires to the Catskills, this is your spot. My Canadian senses were tingling at the top because of the tobogganing potential of this place in winter (which both Whitney and her intern, Maeve, called “sledding” as all other Americans do). I found a nice sense of serenity of there, and I’d recommend everyone takes a moment to take in that viewpoint regardless of the season.

Take a Peek/Attend a Show at the Richard B. Fisher Center for the Performing Arts

The Richard B. Fisher Center for the Performing Arts is an impressive place just outside of Rhinebeck!

I never pass up the opportunity to stand in the shadow of a Frank Gehry building, so that’s why I was all over this, but I also love campuses for higher education,so being on the campus for Bard College was also a treat.

The Richard B. Fisher Center for the Performing Arts (also called just the Fisher Center for the Performing Arts) is a 110,000 square foot structure replete with two theatres, four rehearsal studios, and professional support facilities. It’s also incredibly aesthetically appealing ( at least to me) and worth, at the very least, a drive past. That being said, if you can attend a performance, then do it by all means.

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Where to Stay in Rhinebeck (Rhinebeck Hotels etc.)

There are no shortage of options of accommodation in Rhinebeck, but most do come at a bit of a premium.

The most famous Rhinebeck hotel is the Beekman Arms and Delameter Inn, which claims to be America’s oldest continuously operating hotel. That being said, the Olde Rhineback Inn is also known for its old world luxury, and I’ve heard good things about The Gables of Rhinebeck. I personally was staying at the Rhinecliff Inn, (in Rhinecliff) which is pleasant if you’re looking to be a bit outside of the village of Rhinebeck, but it’s also not for light sleepers as the loud train rolls by with relative frequency.

Anyway, you can take a peek and decide what works for you. As always, I’m just here to help.

What Makes Rhinebeck a New York Getaway Worth Taking?

The village of Rhinebeck is a top notch New York Getaway

What I appreciated about Rhinebeck, and Dutchess County at large (which I’ll be writing more about later), is that it’s very much a “choose your own adventure destination.” You can spend the day visiting the nearby historic sites, stay in the town and stick to the main street’s coffee shops and stores, or do something more adventurous like go for a quick flight at the Old Rhinebeck Aerodrome.

Somehow or another, I’ve developed this love for small towns with a lot going on and, as you may have guessed, Rhinebeck very much fits the bill. So if you’re rolling through, stop for a night and, using this little itinerary, I’m sure you won’t be disappointed.

I want to humbly thank Dutchess County for hosting me as media. All opinions are completely my own. Below, I’d love to know in the comments if you’ve visited Rhinebeck, NY or Dutchess County before and your thoughts! I respond to each and every comment.

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