Visiting Rhinebeck’s 18 Most Instagrammed Places

As part of our series on the most-Instagrammed Places in the Hudson Valley, we present Rhinebeck: known as “a town in Dutchess County.” It’s been home to a range of characters over the last 100 years, ranging from John Astor IV (a millionaire businessman and investor who was born in Rhinebeck and died on the Titanic), Anthony “Fat Tony” Salerno (former head of the Genovese crime family), singer-songwriter Rufus Wainwright, and Jeffrey Dean Morgan of Walking Dead fame who also co-owns a candy shop in town with Paul Rudd.

This list was generated with Instagram geo-tag data of the most Instagrammed locations within the limits of Rhinebeck in the last six months; posts by businesses or business owners were not counted in the tally.

We live all the way over in Kingston and don’t get over to Rhinebeck too often, so we interviewed four local people who know a lot more than we do:

Maggie Myer: The owner of Whistlewood Farm, a rustic Rhinebeck bed and breakfast set amidst a farm with horses, cows, chickens and hiking trails. She’s lived and worked in Rhinebeck for over 30 years. If you’re planning on visiting Rhinebeck, you should stay at Whistlewood.

(NOTE: We designed and built a website for Whistlewood a few years ago).

Jean David Michel: The co-owner of Megabrain Comics, an independent comic book shop that’s been open since 2017.

Michelle Barone-Lepore: Rhinebeck Bank’s VP of marketing and the face of their Facebook video content, which has included a weekly morning show called Wake Up with Rhinebeck Bank.

Carla Goldstein: The Omega Institute’s chief external affairs officer and cofounder of the Omega Women’s Leadership Center.

1. Dutchess County Fairgrounds

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Carla: It’s really wonderful to have the Fairgrounds in our community. It has many interesting events, from arts and crafts to old car shows, but my favorite is the Dutchess County Fair. The tip is to buy tickets in advance, they’re much cheaper that way. Also, while fair food is usually pretty unhealthy, lots of the food vendors are our local restaurants,which makes it a treat. There’s something there for every age. Kids can go to the petting zoo, adults can go to live music concerts.

Maggie: It’s the biggest fair near New York City, and it’s a real country fair. You can see cows, chickens, rabbits, goats, and llamas well as horse shows and tractor pulls. It’s definitely country. They have all of the churches vending and very good food vendors. There’s always a 4-H booth that has the best milkshake in the county too.

Michelle: Rhinebeck Bank is a proud sponsor of the Spork Run at the fair, and also sponsor the app. The fair is focused around food, and the run was created a few years ago to honor the best food at fair. We absolutely adore the Dutchess County Fair.

2. Omega Institute

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Carla: I’ve been working there for 13 years. It’s a spectacular place to work. It brings people from all around the world, including from our own backyard together to learn, get inspired, and feel a sense of community and belonging. Omega is listed in the book 1,000 Places to See in the United States and Canada Before You Die, so if you live in the area, it’s easy to take off your list.

Jean-Michel: It’s a great place. Not only as a Rhinebeck local, you can take advantage of a lot of things, like having a really great lunch or meal there, but the grounds are gorgeous to explore. All year long they have really great and informative little classes and things like that.

Maggie: Omega has grown through the years to become a great wellness center. They have interesting speakers, they have spa services like massage, beautiful gardens, stonework, and a lake where people can go swimming. Everything has to be pre-arranged, you can’t just show up. You have to plan in advance. A lot of people who have plans at Omega stay with us.

Michelle: I love Omega. It’s an amazing place to visit, and it’s so tranquil. There’s farm-fresh food, which is so important to eat. It’s a place that any type of person can enjoy, they offer so much to the public. It’s a destination, a weekend retreat, and you can relax, be yourself and center yourself to face the real world again.

3. Ferncliff Forest

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Carla: What’s famous about Ferncliff Forest is the tower that you can climb and see the entire Hudson Valley. It’s really scary, but I’ve done it anyway, and it’s always worth getting to the top.

Jean: When people from out of town come, and they say they want to go for a hike before lunch, it’s a beautiful walk, light hike for anyone who’s not used to it. You’re not going to be killing them or putting them through bootcamp just to see something pretty. There’s a fire tower to go up and get a 360 view of Rhinebeck.

Maggie: Ferncliff has a lake, and it’s been groomed to be more hiker-friendly. It has a wonderful fire tower that’s been fixed up over the years. They’re building a pavilion to be able to congregate in and do small events, I believe. It’s like Sherwood Forest. Most of the other lands and things we have in the area are more open fields.

4. NY Sheep & Wool Family Festival

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Carla: Going to the Sheep & Wool Festival really brings you back to a time where everything was hand-made. There’s something wonderful about slowing down and connecting to the relationship between people and animals in that way.

Maggie: It’s amazing. It’s definitely country, they have wonderful crafts, people bring their animals. All the food vendors are there also, and it really takes over the town. You can’t miss it. I book a year in advance for it usually.

Michelle: Another incredible event, but I haven’t been. A lot of our customers in Rhinebeck go and absolutely love it. It’s unique.

5. Rhinecliff-Kingston Train Station

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Carla: The station is beautiful, and *maybe* there should be investment in expanding the train station to meet the growing capacity of the Rhinebeck community. But the view of the Hudson River no matter what time of year is beautiful!

Jean: It’s a beautiful old-timey train station. I’ll go there sometimes to walk down to the water with my son, and we’ll just take a little walk through the terminal. It’s this old Frank Capra-esque setting. It’s a great station to go down to the city from, because you don’t feel like you’re taking a train today, you’re taking a train 50 or 75 years ago. That’s kind of fun.

Maggie: People use it, and they come up from the train station. There are always taxis waiting for people to come to town. It’s an old train station. I do recommend renting a car while you’re in town. You can take a taxi to Enterprise and do it that way.

6. The Amsterdam

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Jean: Gorgeous. Winter or summer, they have an amazing menu. It’s thoughtful and comforting, and their back patio where you can eat during better weather, it doesn’t feel like you’re at a restaurant, it feels like you’re at somebody’s house. It’s one of the more gorgeous restaurants that you can eat in.

Maggie: It’s very good, upscale restaurant. I would recommend the little ramekins of duck confit, and chicken livers. It’s all made into a paste, and they serve it with some bread. They have a nice backyard with a bocce area.

7. The Rhinecliff

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Located right by the Rhinecliff train station, The Rhinecliff drew the following praise in 2013 from Design Sponge: “A great restaurant with a veranda for those summer sunsets over the Hudson River. Better yet, stay the night in one of the newly refurbished hotel rooms.”

8. The Beekman Arms

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Jean: The Beek is a great place to get shepherd’s pie or pot pie. It’s definitely worth it to go there to sit at the bar and order some food from their menu, because it’s the ultimate winter comfort food.

Maggie: Great big cocktails. A nice bar crowd in the afternoons and early evening. One of the few places where you can get prime rib on the weekends.

Michelle: A staple of the community, it’s an experience like no other. It really shows the history in Rhinebeck, through and through. So many generations of people have passed through that venue.

9. Wilderstein Historic Site

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Maggie: It’s beautiful, they’ve completely restored it. It’s a beautiful venue. You have to make plans and go at specific times. Wilderstein refers to an old Native American “wild rock” on the property, in German.

Michelle: Rhinebeck Bank is a sponsor of Wilderstein. It’s a preserved land and a great place to visit.

10. Liberty Public House

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Maggie: Great pub with good food, and friendly people.

11. Terrapin Restaurant & Catering

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Jean: Terrapin is fantastic; no matter who is with you, everybody will find something they like and enjoy there. The staff is warm and friendly. It gives you the most bang for your buck. On top of that, if you want to go have a fancy date, you can do that on one side, or if you want to be super casual at the bar, you can do that too. I am a massive fan of Terrapin.

Maggie: Nice-sized portions, farm to table food at a reasonable price. They re-did the dining room. I love the pork chop… it comes with lyonnaise sweet potatoes and spinach, it’s dynamite.

Michelle: If you’re looking for a great date night, or something to do with friends on a Saturday night, Terrapin has incredible food from appetizers to desert. I can’t say enough good things about it. We really love all the restaurants in Rhinebeck.

12. Center for Performing Arts at Rhinebeck

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Carla: We are so lucky to have the Center for Performing Arts in Rhinebeck. It started as an open tent and has grown into one of the most important arts institutions. It’s for all ages, kids, adults, both for performers and audience. More and more, the center is a place that cultivates the artistic talent of the Hudson Valley.

Maggie: Right next door to Whistlewood! Great shows. You could walk to it, but it’s a short drive, an adjacent property and they do a fantastic job.

Michelle: It’s a wonderful place to showcase the arts, and one of the few places to really do this in Dutchess County. It’s a larger venue, and some fantastic artists go there. The performers are seasoned, and they teach actors coming into the field. It’s a beautiful venue, and you wouldn’t expect it from a barn. Anyone should definitely check out a show there. The arts are very important to Rhinebeck Bank. People need an outlet to showcase their talent.

13. Northern Dutchess Hospital

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Carla: So many communities don’t have a hospital within ten minutes of where one lives, so we’re really lucky to have a hospital nearby, especially with the recent renovation and updating of the hospital. One of the great things about it is that doctors have moved their practice into the building itself, so it’s become kind of a community health center. You can go there for a doctor’s appointment or physical therapy or emergency care. It’s an unusual benefit to have all of that so close and consolidated under one roof.

Maggie: It’s a nice little hospital. I know they have a reputable physical therapy program.

Michelle: First of all, it’s absolutely beautiful. It’s a gorgeous facility that has state-of-the-art healthcare. The Birthing Center is beautiful. A lot of women prefer to go there than any other hospital because of what they offer. The treatment that you receive there is great. I think it’s a hospital that stands alone because of the attention they pay to their patients.

14. Bread Alone

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Michelle: Who does not love Bread Alone? The bread is fantastic, their lunch is amazing. The people behind it are so compassionate about the community, which is important. It’s really become a big brand that started there. They’re sold at so many different grocery stores and such a staple of the community.

15. Rhinebeck Bagels & Cafe

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Jean: In terms of insider info, instead of going anywhere else for breakfast or lunch, just go to Rhinebeck Bagels. They have the most amazing breakfast or lunch menu. If you want to get the “real feel” for the people of Rhinebeck, that’s the water cooler.

Michelle: The bagels are delicious. The only problem is I like to eat too many when I’m there. Another staple in the community, and a must try for breakfast. I know a lot of folks love that venue.

16. Southlands Foundation

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Maggie: Good for horseback riding for children. It’s a nice farm just south of Rhinebeck. There’s also Welwyn Farm up the road from me, which is closer, but you need reservations way in advance.

17. Drayton Grant Park at Burger Hill

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Carla: Just about every kid in Rhinebeck learns how to sled on Burger Hill. Adults love to go to the top to watch the sunset in good weather. It’s also a great navigational mark; you know where you are in relationship to Burger Hill.

Maggie: The best view of the Hudson Valley, and it’s two miles from Whistlewood. The Winnakee Land Trust does great things there, they do moon hikes, and lots of different low-key events there.

Michelle: The sites and views from Burger Hill are fantastic. We shot a video there with the folks who work at the Rhinebeck branch. If you’re looking for a nice walk with someone you love, it’s a beautiful place to go, and take your dog up there.


The Rhinebeck Aerodrome

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Carla: I’m a bike rider, so I ride by the Aerodrome very often. One can get the pleasure of seeing the show inside and outside the aerodrome. It’s a surprising attraction in the middle of a rural, residential community. It’s another one of those things that puts you in touch with the history of flight. It’s intriguing to see the evolution of airplane technology. You can see the planes doing tricks from miles away. Going is really fun too.

Jean: I haven’t been there, but I know they have a really cool steampunk festival that I can’t wait to go to this year.

Maggie: Fantastic, that’s also about a mile or two up the road from me. Great shows, seasonal.

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