Hudson Valley Winter Getaway guide

February 8, 2019

“So are babymoons a thing?” That’s what the owner of our Airbnb rental asked us while we checked in to his Upstate NY home. We laughed along with him at the notion of this recent trend that has popped up over the last few years, which we gladly used as an excuse to get off the grid for a few days. We have a list of places we’ve been wanting to travel to but with me being close to the end of my second trimester and us keeping a post-holiday season budget in mind, Mike and I decided to venture somewhere closer to home.

Though I’m from Long Island and grew up taking occasional trips to Upstate NY, I hadn’t been back in years, nor had I really explored what any of these towns had to offer. If I couldn’t lay by a beach with a virgin mojito in hand, than I wanted a weekend full of fireside hot cocoas and all the meals my foodie heart desired. So the Hudson Valley it was, and with a tentative plan in place, we headed up north for our little winter getaway. Below is what ended up becoming our three-day itinerary!


Our Airbnb was about 20 minutes from Rhinebeck, and since we couldn’t check in to the barn until 3:00pm, we decided to hit up the town for lunch and to gather a few provisions for the weekend.¬†The Amsterdam was our first stop in this adorable little town, where we both ordered the lunch special. My buttery brioche grilled cheese and garam masala butternut squash soup kick was heavenly, but my favorite thing might have actually been the Ginger Snap, a jalapeno and mint infused mocktail. One of the best drinks I’ve had in awhile, even if it left out the buzz ūüôā¬†

I also proclaimed to Mike that this weekend would be known as the “weekend of carbs” as I planned on trying every piece of delicious bread and pastry I could get my pregnant hands on. So off we went to check out¬†Bread Alone, where we picked up some extra flaky croissants and a whole grain loaf (because #balance) to keep at the house for the weekend. We’d make a point to come back in though since their cafe menu was right up our alley.¬†

The rest of our Thursday was spent settling into our dreamy rental for the weekend (like even better than the pictures listed online kind of dreamy) and cooking up some braised short ribs for dinner. With no TV in the house, we queued up the Binge Mode podcast to refresh our memory on “Game of Thrones” (HIGHLY recommend if you’re a fan – very informative and also hilarious) and worked on our 1,000 piece puzzle until bedtime.¬†


We decided to sleep in and spend the morning at home, before venturing up to Hudson, about a 25 minute drive north of our Airbnb in Red Hook. Our friends Betsy and Tim had recently spent a weekend there and sent along a list of recommendations we kept in hand. With a 14 degree forecast though, our walking portion was pretty limited so we did what we did best – eat, drink, and eat some more. And our plan was perfect for a quaint town that was full of amazing eateries and locally owned shops. Plus, I needed wool socks because, well, it was 14 degrees (and I apparently didn’t pack appropriately for that)!

Enter Hudson Clothier, a reasonably priced apparel shop full of American made goods (and run by a local woman) that I instantly fell in love with. Mike and I left with my new socks in tow, and a lunch recommendation from the owner, Mary (“Go to Oak and get the oven roasted olives. They’re out of this world.”) so we did just that.¬†

So began our food and beverage tour through Hudson. A Neapolitan pizza and oven roasted olives at Oak Pizzeria, a sampling of local beers for Mike at Hudson Brewing Company, as well as his go-to cocktail order, an Old Fashioned at American Glory.


But the highlight of our already amazing tour through Hudson went to the last stop of the day, our meal at Backbar. Tucked away on Warren Street, this eclectic hidden bar/restaurant/antique shop blew us away with their southeast Asian menu. We sat at the bar, savored every last bite of our order (listed below because it was that insanely good), and started pitching the idea of bringing Backbar to Philly to the manager, who happily chatted with us throughout our meal. He even convinced Mike to try broccoli for once in his life (“Dude, I hate broccoli and I think it’s f**king delicious. Order it.”) – and Mike LOVED it. So if you go, make sure you order these!

Salt + Pepper Broccoli

Shrimp Pancake 

Beef Eggroll

Dry Fried Greenbeans

Dan Dan Noodles 


Saturday morning we contemplated if we should cancel our plans so we could head back up to Hudson for Backbar’s Weekend Dim Sum Brunch. That was literally how much we loved our meal. But alas, we decided to stick with our itinerary, which included a day of relaxation and more to explore. Kingston, a historic city for creatives, sat just across the Hudson, and Rhinebeck was conveniently situated along the route we needed to take. We kicked off our morning with massages at Rhinebeck’s Rain Spa, whose decor and design appealed greatly to my affinity for global chic vibes. Also, is there anything better than when spas are stocked up on delicious treats and beverages? I don’t think so. After 90 minutes of getting our kinks worked out, we layered up and headed into Kingston for brunch at Duo Bistro.¬†

What I loved most about this spot was their seasonal menu, and I am seriously contemplating trying to figure out how I can whip up the turkey confit and sweet potato hash meal I scarfed down that day. Just down the block sat Rough Draft Bar + Books, which is a must to stop at if you are a. book nerds like us and b. enjoy beers like us. I honestly could have hung out at this place for hours, and it was no surprise to see many people cozied up on their own or with friends around the space. 

The last place on our must-sees list in Kingston resided about 2.5 miles east, in Kingston’s Waterfront District. A friend of mine from high school suggested we stop in for a drink and some snacks at Brunette, the most chic little wine bar I’ve ever visited, and also check out local shops Clove + Creek and Hops Petunia.¬†It was the perfect way to end our cold and quiet afternoon before heading home to sit by the fire and ensure we had enough time to finish that damn puzzle that stared us down from the dining table.¬†

And just like that, our winter babymoon came and went. Mike and I grabbed one last carb heavy meal (NY Bagels – duh) before packing up our stuff and saying farewell to our home for the weekend. We’ll be back though, and you should check it out too! Below are additional resources and tips to consider when planning your trip up north!


And North Blog РSuper helpful and also so visually pleasing. A curated guide to Upstate NY. 

There are more and more adorable little hotels and B+Bs popping up in the Hudson Valley area but we opted to go with this rental. So many amazing and quaint Airbnbs to explore up near the Catskills.

Something to consider when planning your trip. Some stores were either closed for the winter season or only open during limited times throughout the weekend. If there are specific spots you have in mind that you want to check out, make sure to look up their hours or call ahead!

Other spots on our list we didn’t get to check out but read and heard amazing things about: Fish + Game (Hudson),¬†WM Farmer and Sons (Hudson), Stockade Tavern (Kingston), Hillrock Estate Distillery (Ancram)



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