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  • Writer's pictureSusan Benz

A Fall Weekend Getaway in Hudson Valley & NYC: Rhinebeck, Roosevelt, and the Rockettes

The snow, sleet, and blustery weather this week has me reflecting on a weekend getaway I took a few weeks ago to visit my daughter, Lacey, in NYC. It wasn't exactly a "tropical destination", but it was certainly a nice break from the freezing winds and winter weather that we are having in Minnesota. Just this week, we woke up to six inches of snow on the ground. My husband, who still has about 200 acres of corn left to harvest, was not happy with Mother Nature's Thanksgiving gift! 😱🌬


Instead of sightseeing in Manhattan, which I have done other times with Lacey, we decided to rent a car from LaGuardia Airport and spend the weekend exploring Hudson Valley. It was a refreshing break for the both of us: Lacey, from the hustle and bustle of Manhattan, and I from the craziness of harvest on the farm.


To be honest, I was slightly nervous about renting a car in NYC, but it was no big deal! I would recommend having a passenger that can navigate as you drive along because the toll lanes and exit signs get confusing when you combine that with the traffic, yet overall, the driving was no different than any other large city. And, it was so convenient to have a car throughout the weekend. We definitely covered more ground than we would have if we had been limited to public transportation.


*Tip: Make sure to research what discounts you are eligible for when renting a car for your weekend getaway! For example, Delta has a promotion with some auto rentals where you earn SkyMiles for each vehicle that you rent. I know that some corporations, like Lacey's firm, have a corporate employee discount you can apply to your rental too. Check these out before booking to save money!


Our first stop out of NYC was Tarrytown, a quaint town along the Hudson River with a bustling Main Street. Of course, my main reason for stopping there was the yarn shop! 🧶😍 The Flying Fingers Yarn Shop in downtown Tarrytown had a great assortment of hand-dyed yarns and knitting/crocheting accessories. I wish I would have brought another suitcase just for yarn! Along with a stop at the yarn store, we enjoyed a cup of soup at the Muddy Water Coffee & Cafe before venturing north to Rhinebeck.


We didn't get to Rhinebeck until late in the evening, nevertheless, we were blown away by our first impression. I understand why Rhinebeck has earned the title as one of the "18 Most Charming Small Towns in America." The twinkling lights that adorned Main Street were so pretty, and the street musician on the corner definitely added to the ambiance. The town has a few streets of local clothes, jewelry, and food shops, in addition to a wide variety of top-notch restaurants and bars. After checking into our accommodations, we had dinner at Terrapin Restaurant along Main Street. The food was good, and our service was quick and efficient, even though it was a busy Friday night.


*Tip: You are strongly encouraged to make dinner reservations when visiting Rhinebeck on the weekend. Regardless of the season, our B&B host said that Rhinebeck gets very busy on the weekends, and it is difficult to find restaurants with availability. We noticed this when leaving Terrapin, as the line was practically out the door! You can find casual places to eat without a reservation, but if you are planning on enjoying some of Rhinebeck's culinary hot-spots, be sure to book in advance!


When planning a trip, most people choose a location first, followed by reserving accommodations of some sort (lodging, Airbnb, bed & breakfast, etc.). Lacey and I went against the norm and found a B&B to stay at before considering the location... It just worked out that we were only a few miles away from charming Rhinebeck! Lacey specifically wanted to stay at a B&B, preferably on a farm, during our weekend getaway. This significantly narrowed our choices, making it relatively easy to pick a place. I am happy to report that Whistlewood Farm Bed and Breakfast exceeded our expectations!


Whistlewood Farm is an adorable bed & breakfast run by Maggie, a thoughtful and caring hostess that tended to our every need. When we weren't eating a slice of Maggie's fresh pie or enjoying farm-fresh eggs for breakfast, Lacey and I fed apples to the horses, had fun watching the chickens, and hiked along Maggie's well-groomed trails.


Our "Sweet Violet Room" was comfortable and clean, and we really enjoyed meeting our fellow guests throughout the weekend. One couple was particularly friendly, and we even exchanged information at the end of our stay. I love how B&Bs are more personable than big-chain hotels. It is always fun to make friends and exchange stories with other travelers, even if it is just for a quick weekend.


*Tip: Stay at a bed & breakfast if you are visiting Hudson Valley! The region is known for its unique B&B accommodations, and I highly recommend you take advantage. Whether it is on a working farm, like us, or in a historic inn, there is bound to be a place that fits your budget and travel plans. Plus, you will be served a freshly cooked homemade breakfast - the best perk of staying at a B&B!


The Vanderbilt Estate

On Saturday, we spent most of the day gallivanting around the Hyde Park area of the region. My sister-in-law was adamant that we visit President FDR's estate, so we had to check it out. We also explored the Vanderbilt Estate. Both of these historic mansions are within a five-minute drive of each other, so it made for convenient sightseeing.



President FDR's Estate

We thought that the estates would have been prettier in the summer or fall when the flowers were in bloom or the leaves were changing color. November is a pretty "dead" time of year in upstate NY. It was still fun to see the houses though, and both places are managed by the National Park Service, so if you have an NPS Passport Book (my daughters do!), you can stamp two more locations.




*Tip: If you want to visit the inside of the mansions, you have to join a guided tour. These cost money ($10/pp for Vanderbilt and $10/pp for FDR's house (+$10 if you visit the Presidential Library and Museum) and depart at scheduled times, so plan in advance if this is what you are looking for. Lacey and I are not necessarily "tour folk," and we preferred to walk the grounds and save our money instead. We also timed our visits poorly...it would have been a long wait before the next tour left. Plan ahead if you want to see the inside!


As we drove south along Highway 9, we visited The Culinary Institute of America. It is on my bucket list to return and take a culinary class someday! The campus was beautiful and very visitor-friendly. We walked in the main building, checked out the gift shop (a chef's paradise!), and had a nice chat with a current student. It is so much fun to hear about studying culinary arts at the undergraduate level. This student said that her major included an "Italian Food Concentration" - how fun!



There are restaurants at The Culinary Institute too if you want to extend your visit. Most of the restaurants encourage reservations, but there is also a casual cafe (open during weekdays) and Tavern Restaurant in case you don't want to make reservations ahead of time. The student we spoke with recommended the family-style Pasta Dinner at Ristorante Caterina de' Medici on campus. It sounded delicious! I'll add that to my bucket list too... right next to the culinary class. 👩🏼‍🍳🤩


Even though Lacey and I originally planned for this weekend to be one of rest and relaxation (RE: crocheting by the fireplace), we had too much that we wanted to do! The rest of our Saturday was filled with yarn shopping and chocolate tasting. I can't think of a better way to spend my weekend! On our hunt for Hudson Valley's neatest yarn shops, we visited the Hudson Valley Sheep & Wool Co. This store is on a sheep farm in the countryside near Red Hook, NY. It was cool to see the sheep running in the pasture and then watch the employees spin the wool: a truly "farm to hook" process!


Back in Rhinebeck, we strolled along Main Street, popping into stores and enjoying the charming atmosphere. Lacey's favorite shop was Oblong Books & Music, a local bookstore with a selection that rivaled Barnes & Noble. I, on the other hand, loved the chocolate shops in Rhinebeck. This small town of 8,000 people had THREE chocolatiers. I was in a chocolate-lover's paradise! I think I almost spent more money on chocolate and yarn this weekend than my flight to NYC (haha, just kidding). Regardless, it was fun to explore the town after a long day of adventuring through the Eastern Hudson Valley region.


Even though Maggie, our B&B host, had more than enough desserts to satisfy us both for dinner, we figured that we probably needed something with some nutritional value, so Lacey and I headed to Savona, an Italian restaurant in Red Hook, for the evening. If you are looking for tasty Italian with a wide variety of options and hearty portions, it is a great choice! We just split appetizers, but the service was fast and the food was fresh.


On Sunday, we were sad to leave Whistlewood Farm and Rhinebeck behind. Our weekend flew by! Lacey was especially bummed to say "goodbye" to fresh air, green spaces, and starry nights. Since we drove on the east side of the Hudson River up to Rhinebeck, we decided to drive back on the west side. This side was not as picturesque as our drive on Friday, but we still passed through a few cute towns and had a great view of the river.


Plus, if you choose to drive south on Highway 9W from Rhinebeck, you will drive right past the West Point Military Academy. For us, this was the perfect time to stretch our legs and take a quick look around campus. Once again, we opted out of the $20 guided tour and just walked through the exhibit hall and gift shop instead. We wish we would have had more time to explore the campus, but we wanted to get the car returned at La Guardia before we had to pay for another 24 hours of rental.


Back in Manhattan, we capped off our weekend with a quick visit to some of the City's top Christmas highlights. My favorite stop was the Bryant Park Holiday Village. Bryant Park is typically a 9.5-acre park directly in the middle of Manhattan (just blocks away from Times Square and Grand Central Terminal!), but for the holidays, it is transformed into a Christmas market reminiscent of a traditional European holiday market. There were over 175 different vendors selling anything you could imagine: jewelry, artwork, clothing, and food. The food options were plentiful, with lots of unique options that you could only find in NYC.



*Tip: Bryant Park also has a large ice skating rink that rivals the popular Rockefeller Center rink. The rink was packed when we visited (except for when the Zamboni resurfaces the ice 😋) ... and that was on a Sunday night in the middle of November before the holiday tourists arrive. I would strongly suggest reserving your skate time online or going in the early morning/late evening on an off-peak day. Any creative way to avoid the crowds will be rewarded!


After visiting the Bryant Park rink, we walked over to the Rockefeller Center rink to compare crowds. This ice skating rink was also very busy, but we enjoyed watching the skaters before ending our night with the classic NYC holiday experience: The Rockettes' Christmas Spectacular!


I wasn't sure what to expect when we bought tickets for the show. I think this was good because then I went into the show with no expectations... which the show greatly exceeded! From the moment we lined up for security, we were transported into a winter wonderland. The greeters were in festive costumes, the lounge areas were adorned with Christmas decor, and Radio City Music Hall was dazzling with lights and holiday cheer. The performance was everything that one would imagine from the Rockettes: extravagant dance numbers, a full orchestra, two organists, a complete dance ensemble, and live animals. It was a great family-friendly way to celebrate the holidays, and it certainly put us both in the holiday spirit! (Although, that also brings anxiety because time is quickly vanishing to plan holiday meals, wrap presents, and order Christmas cards... I will have to keep chanting 'peace and joy' to maintain my sanity these next few weeks 😳🙏🏻🧘🏼‍♀)



*Tip: Research online for discount codes before booking tickets to the Rockettes' Christmas Spectacular. I know that there are discounts for Chase credit card holders, and quite a few companies have employee discounts too. I also saw reduced priced tickets on Groupon when I was ordering our tickets, so there are definitely ways to save money for the show. With up to six shows a day in a 6,000+ person theater, it makes sense that they are discounting tickets to sell out each show!


It was sad to say goodbye to Lacey on Monday, but back to "all the things" for both of us: work, church/civic commitments, and household chores. It was so nice to have a break for a weekend, and I couldn't think of a better place to spend it than Rhinebeck and the Hudson Valley region. As I continue practicing weaving more peace and joy in my life, I am fortunate for weekends away like these. Time spent with family (away from screens, notifications, and distractions) always refreshes me. I hope that some of these tips and insights help you plan your next weekend getaway to upstate NY so that you can also enjoy a time of rest!


I'd love to hear from you, too. Have you ever been to the Hudson Valley region? Or, have you ever stayed at a bed & breakfast? Lacey and I are always looking for recommendations for our next weekend getaway!

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