Planning a trip to one of New York’s prettiest regions? Here are all the places to visit in Hudson Valley I managed to see on my first trip!

When someone refers to the Hudson Valley region of New York, they’re referring to the area that surrounds the Hudson River between Albany and the top of Manhattan. That’s 150 miles (241km) and 10 counties!

While you could drive through in a little under 3 hours, I’m assuming you clicked on this post because you intend on stopping around to check out the various small towns, landmarks, and outdoor spaces. There’s a lot to do and even after numerous visits, I’m sure someone could still find more to do.

I knew I was coming home through Hudson Valley on my way back from a month long road trip up to Massachusetts, and I wanted to take some times to get to know the region better. You’d think since it’s only a 2 hour drive from where I am in Pennsylvania that I’d have come before, but really this was my first time!

Anyway, here are all the pretty places I managed to visit with the week and a half I had!

Places to Visit in Hudson Valley from North to South

Millerton - Places to Visit in Hudson Valley

1. Millerton

  • Parking: A lot of side streets have free parking and there’s a lot right by Harney & Sons.
  • Stay: I only stopped in but if you want to stay here, The Millerton Inn looks cute

Since I was coming from Connecticut, the first place I stopped in Hudson Valley was the very cute small town of Millerton. It’s been around since the 1800s and named after Sidney Miller, the guy who brought the railroad here. You might also recognize the town because Daryl Hall of Hall & Oates called it home for a while! He even produced some of his show, “Live from Daryl’s House” from here.

Since I was coming from Washington, CT and had plans on staying over in Hudson, Millerton was the perfect in-between stop. Plus, after being gifted some Harney & Sons tea, I knew I had to stop in to their flagship shop!

This town is honestly great for a full day trip but also you can fit in a lot if you only have a few hours. After getting some tea and food at Harney & Sons, I also got a green tea matcha at Irving Farm New York, and then perused the many, many books at Oblong Books.

If I was staying over night, I’d have loved to try Oakhurst Diner for dinner and maybe gone for a run along the Harlem Valley Rail Trail. There aren’t many accommodation options in town but the Millerton Inn looks adorable and is right on Main Street.

Hudson - Places to Visit in Hudson Valley

2. Hudson

  • Parking: The street next to Nautical Nest has free parking, you just have to keep an eye on when it switches sides.
  • Stay: I really liked Nautical Nest Hotel Hudson. Felt more Airbnb than hotel with lots of space and a nice little communal kitchen nook.

Next up on my drive was the aforementioned Hudson. My friends over at Bobo & Chichi recommend staying longer here and Kingston, so I stayed overnight.

Hudson is much larger than Millerton, but really none of these towns will feel overwhelming while you’re exploring. It’s situated on the right side of the Hudson River and made a name for itself when it became both an artist enclave and big LGTBQ+ destination. Even in the short time I visited, I felt this sort of hippie, quirky vibe and I feel like this would be a really fun spot to return to for a longer weekend!

Anyway some of the places I went were feast & floret for the later opening times and Italian dishes, Spotty Dog Books & Ale to peruse their book selection, stationary goods at The Social Type, and coffee at Wyld. Mostly I had fun just walking around Warren Street and over to the waterfront.

Olana Historic Site - Places to Visit in Hudson Valley

3. Olana State Historic Site

  • Parking: Right by the visitor center
  • Stay: Nearby in Hudson

Before you fully leave Hudson, drive over to Olana State Historic Site. It was one home to one of the Hudson River School painters, Frederic Edwin Church, and the design is a mix of Victorian and Exotic Revival. (Think – obsession with what Westerners back then thought of as the Far East). That’s why it looks like there’s sort of Middle Eastern and Moorish design elements on a home built in upstate New York. The name apparently even comes from an estate in ancient Persia.

Even if tours for the interior are done of the day, you can still walk around the outside and take in the views! It’s a pretty big park, so you could bring something to eat and hang out around the exteriors and take in the view.

Saugerties Lighthouse - Places to Visit in Hudson Valley

4. Saugerties Lighthouse

  • Parking: There’s a parking lot at the entrance and then you’ll have a bit of a walk to get to the actual lighthouse.
  • Stay: At the lighthouse!

Crossing over the river, I initially wanted to spent a few hours at in the town of Saugerties. However, I was short on daylight and had plans to stay in Kingston for the night, so I only had time for a quick stop at Saugerties Lighthouse. This version was built in 1869 and is even a bed and breakfast if you want to stay over.

I wouldn’t say this lighthouse is an absolute must-see and if the weather is bad, I wouldn’t take the time to walk along the path to get there. But if you want a quick stop on your way down the region, it’s a pretty little lighthouse. Plus if you come earlier than I did, you’ll be able to do a tour.

Kingston - Places to Visit in Hudson Valley

5. Kingston

  • Parking: I stayed at an Airbnb a little away from the main part of town and it had its own drive way. In town, it’s mostly paid parking but I did manage to find a free parking spot on either Crown or Green Street.
  • Stay: I stayed in an Airbnb that was out of the main part of town and not that great of a location. If I went again, I’d stay at Hotel Kinsley.

Next was the very pretty town of Kingston! Kingston is one of the bigger towns in Hudson Valley and was actually New York’s first ever capital city! It has three distinct historic districts – Stockade, the Midtown Neighborhood Broadway Corridor, and the Rondout-West Strand Historic District.

I stayed mainly around the Stockade District. Partly because of where I parked and also because I was dying to visit Rough Draft Bar & Books. It’s by the Four Corners, the only spot in America where you can see four pre-Revolutionary buildings. You can also see Ulster County Courthouse, which is where Sojourner Truth became the first Black parent to win a case and save her son from slavery. And, of course, don’t miss the pastel facades on Wall Street!

6. Innisfree Gardens

  • Parking: Has its own lot.
  • Stay: I went further to Hyde Park, but if you want to stay in a town nearby, look to Salt Point or Millbrook.

Despite the rainy weather, I was determined to keep my reservation at Innisfree Gardens and enjoy them! I grabbed some lunch at Joe Beez’s in Kingston and brought it with me to eat at one of the picnic tables. It would’ve been the perfect day to relax and read and walk the whole roundtrip path if it had been sunny! I did my best using my umbrella to cover my lunch and my Kindle lol.

Even in the rain though, it was quite beautiful. And, on the plus side, only two other people were also crazy enough to be out in the garden with me, so it really felt like we all had the place to ourselves. While I didn’t do a full loop, I did manage to go the main gardens and enjoy the pretty views.

7. Springwood in Hyde Park

  • Parking: Plenty of space at visitor center
  • Stay: This Airbnb nearby – Dot is such a lovely host!

Another one of the unmissable places to visit in Hudson Valley is Springwood, aka the home of Franklin D. Roosevelt. It’s in the town of Hyde Park, which is also near the Culinary Institute of America. If the weather had been nicer, I would’ve tried to go to one of their restaurants for dinner, but it was so cold and dark and my Airbnb was so cozy and warm, I ate my leftover sandwich and stayed in for the night.

Anyway, I went to Springwood the next day when the weather was much nicer, and I loved walking around and learning more about both FDR and Eleanor. FDR has an interesting legacy, but I seriously loved learning more about Eleanor and all the ways she revolutionized what it meant to be a first lady and public figure.

There’s a museum and you can tour Springwood itself. I just opted to check out the museum and saw the exterior of the house as well as both FDR and Eleanor’s final burial place.

8. Val-Kill

  • Parking: Plenty of space in a sort of field by the house.

I had to be at the next spot on this list for a tour, so my visit to Val-Kill was short, but I wanted to try to make sure I at least visited what was Eleanor’s actual residence. This former furniture factory was her personal retreat and she lived here full time after FDR died. If I get a chance to come back, I’d like to do one of the tours. Eleanor really is that girl and I can never learn enough about her and how she much she managed to accomplish despite her limitations as a woman in the early 1900s.

I think my favorite fact was how as soon as her husband died, she was vocally and publicly supported the Civil Rights movement. Like he died in April and by May she was on the board for the NAACP!!

9. Bannerman Castle

  • Parking: I believe Scenic Hudson’s River Center had free 3-hour parking, and I cut through to get to the dock for the Bannerman Castle tour. There’s also a parking lot for the docks but it was packed for some festival when I went.
  • Stay: Nearby in Beacon

Bannerman Castle has been on my bucket list ever since I made this castles to visit in the US post years ago. It’s just such a curious creation! Located on Pollepel Island, it was built to hold military surplus. Its owner, Dundee-born Francis Bannerman VI, literally built a castle as a form of advertising for his business. I kind of love that his family would also use the castle during the summers. Like imagine being a kid just running around a random island with a castle storing a bunch of ammunition! His wife’s gardens are also still intact to this day.

The reason the castle looks more like ruins than castle is because of a fire in the late sixties.

To visit, you have to book one of the tours which meets in Beacon and takes you on a boat ride on the Hudson to the island. There you’ll get a little tour and then some free time to wander around before boarding the boat back. I’d pack a lunch since their snack bar is kind of limited and expensive.

10. Beacon

  • Parking: You can park overnight for free on the main street but there are also some public parking lots if you can get a space.
  • Stay: The Dutchess Inn & Spa – right on Main Street and very cute. Don’t forget to check out their rooftop.

It’s well worth staying overnight in Beacon if you visit Bannerman Castle. This tiny town is adorable and backs a lot to do in such a small space, I was kind of surprised! All along Main Street you’ll find cute little cafes and fun boutiques like Blank Square Coffeehouse or Colorant. I actually picked up a diffuser from Lewis & Pine that’s still going strong in my bathroom after all these months.

If you have time, check out the Dia Beacon, which focuses on natural light and modern art. I wanted to go but it was closed when I was there (it’s only open Saturday – Mondays).

11. Armour-Stiner Octagonal House

  • Parking: There’s limited parking on the lawn in front of the house.
  • Stay: Over in Sleepy Hollow or Tarrytown.

Before I made my way to Sleepy Hollow, I had to stop into the Armour-Stiner Octagonal House. It’s looks like my dream doll house with its pink Victorian architecture! It’s actually one of the only domed octagonal residences in existence and was inspired by Donato Bramante’s Tempietto in Rome. I highly recommend booking a tour to go through the house’s history and to see everything inside. I actually loved the Myths & Mysteries tour but they have all sorts of themed options. Seriously one of the most unique places to visit in Hudson Valley and New York in general!

12. Sleepy Hollow & Tarrytown

  • Parking: My hotel had parking and then I managed street parking for the most part. Some of it was free, some of it costs maybe $2-3 for a few hours.
  • Stay: Tarrytown House Estate on the Hudson

I mean considering I was visiting Hudson Valley shortly before Halloween, it would’ve been extremely bad taste to skip out on Sleepy Hollow and Tarrytown! After all I’m still haunted by that “Hey Arnold” episode…

I’m not really sure where Sleepy Hollow begins and Tarrytown ends, but the reason I put them together is that they’re kind of mixed and considered villages, not towns. There are a lot of cute little things to do while you’re here but know that everything is kind of spread out.

Definitely check out the Sleepy Hollow Lighthouse and walk enough that you can see this long, colorful mural. You can also poke around Sleep Hollow Cemetery to say hi to Washington Irving. Coffee Labs and Muddy Water had some great coffee and Sleepy Hollow Bookshop is cute, albeit more for kids and young adults. If you stay at the hotel I did, I recommend splurging on Goosefeather for dinner. It’s like fancy Chinese and so, so delicious.

Lyndhurst Mansion - Places to Visit in Hudson Valley

13. Lyndhurst Mansion

  • Parking: Free lot on property but you’ll probably drive around to see the full grounds anyway.

To finish off this list of places to visit in Hudson Valley is also one more place to visit in Tarrytown – Lyndhurst Mansion. I’ve also had this place on my list thanks to that US Castles bucket list, so I knew I had to go while I was here. It’s got a cool Gothic Revival design and was once owned by Jay Gould. You might also recognize it from “The Gilded Age” and I, of course, recognize it from Winter’s Tale, a movie no one seems to remember but I do.

I didn’t get a chance to go inside because it was closed the day I went. However, you can still book tickets to drive and walk around the grounds which are quite massive themselves.

And there you have it – all the places to visit in Hudson Valley if planning a road trip. Any places I should add on future trips? I can’t believe it’s only 2 hours from me and this is my first time!

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