Your Itinerary for a Hudson Valley Weekend Getaway

If you have never been to a bed and breakfast, or just aren’t familiar with our amazing part of the state, maybe we can initiate a planning frenzy with your itinerary for a Hudson Valley weekend getaway. It doesn’t matter where or what you are trying to escape, whether it’s a weekend getaway from NYC or from a couple of rambunctious toddlers! Come to Caldwell House, and let us help you imagine your fabulous flight from your day-to-day responsibilities.

Our buildings may be historic and built while Thomas Jefferson was president, but our amenities and services are completely up to date. Booking a room is easily accomplished online, but if you have questions, we are happy to help with your plans! 


We make it both super easy and safe at the same time! All instructions will be emailed to you 2 days before arrival. All you have to do is show up anytime after 2:00 pm. Come in and check out the front porch and the Front Room. Notice the elegantly curved back wall and marble-trimmed coal-burning fireplace. Visit the Parlor, where the original owner and his family relaxed over 200 years ago. Aren’t your shoulders relaxing just a bit?

Now to your room, immaculately clean, with a totally modern bathroom, plush bathrobes, and comfy reading chairs. Log in to the WiFi (are you really going to work this weekend?), take a deep breath, and start to relax! Maybe you have asked us ahead of time for a bottle of wine, and there it is waiting for you, along with wine glasses and a corkscrew. Sit down and have a glass!

Dinner plans

Depending on the time of your arrival, you may still want to enjoy dinner out. Right next door to Caldwell House is, no surprise, an Irish pub! Stop over to Loughran’s for a nice relaxing casual dinner. If you are up to it when you return, check out the board games in the front room, and begin a challenge that may last all weekend.


Depending on where your room is located, you may smell breakfast long before it arrives. We are currently delivering a hot breakfast basket to your room at 9:00 am and will pick up the basket at 10:15 am. If you have any special needs or restrictions and have told us ahead of time, you will see them reflected in the basket. Stay tuned, as safety precautions change, we hope to return breakfast to the Dining Room or Great Room in the future.

Outings for the Day

The first stop for the day is a tour of the West Point campus. See some great views of the Hudson Valley, and get a little history lesson, since the Academy began in 1778. 

The day is beautiful, so after the tour, take a drive and visit a couple of wineries on the Shawangunk Wine Trail. Maybe a stop at Angry Orchard, for some cider, and then a visit to Brotherhood Winery, America’s Oldest Winery. If you are hungry after your breakfast, grab a Charcuterie Board at their restaurant, or maybe a Pork Belly Bȧnh Mi. Don’t eat too much, for you have dinner plans at a great restaurant.

Dinner Plans

Tonight you have reservations at Blue Pointe Restaurant, one of our recommended fine dining choices. With an amazing view of the Hudson River, and many choices of seafood, meat, and vegetarian. There is also a varied choice of cocktails and wine. Back to your room for another night on luxurious linens and a relaxing atmosphere.


Day 2 and another amazing, but completely different breakfast basket waiting outside your door at 9:00 am. If only I could get a delivery like this at home!

Outings for the Day

Time to pack up for an 11:00 am check-out. Our day isn’t over, we have a visit to the Storm King Art Center! With the sun shining again, a stroll through the myriad of sculptures is a perfect way to spend an hour or two before we head back. But wait, there is so much that we haven’t done! There are hikes, kayaking, and balloon rides!

What an amazing weekend! And still so much left to do! Clearly, your itinerary for a Hudson Valley weekend getaway needs to be set on repeat. And soon! Don’t worry, Caldwell House will be here waiting for your return.


Leave a Reply

Your email address will not be published. Required fields are marked *