Things to Do in the Hudson Valley: My Insider Guide
- Katie Hamuka
- Jun 24
- 5 min read
Updated: Jun 30
Top Hudson Valley recommendations for a romantic weekend away? Honestly, I get this question all the time.
I've worked in the area for years now. I've done the touristy stuff, found the hidden gems, and collected all the details so you don't have to.
Here's what I actually recommend when people ask me about things to do in Hudson Valley.
Outdoor Stuff That's Actually So Fun
Walkway Over the Hudson (Poughkeepsie/Highland)
Address: 61 Parker Ave, Poughkeepsie, NY 12601 Phone: (845) 454-9649 Website: walkway.org
This bridge is legitimately cool.
I was skeptical the first time - like, it's just a bridge, right? Wrong. It's 1.28 miles long and you're walking above the Hudson River. The views are insane.
Pro tip: Don't go on weekends in October unless you enjoy crowds. Go early morning or sunset instead, way more romantic.
They have goats there now doing landscaping which is random but cute.
Poets' Walk Park (Red Hook) - breathtaking views of the Hudson Valley
Address: 776 River Rd, Red Hook, NY 12571
Website: scenichudson.org/parks/poetswalk
This place inspired Washington Irving, apparently. And honestly? Same.
It's good for picnics and the pavilions are perfect when it's drizzling - which happens more than you'd think up here.
My dog loves the trails. Fair warning though - no dogs allowed in some sections during nesting season.
Artistic Places to See
Storm King Art Center (New Windsor)
Address: 1 Museum Rd, New Windsor, NY 12553 Phone: (845) 534-3115 Website: stormking.org
This place is 500 acres of giant sculptures just sitting in fields and hills. It's different and beautiful and unique, for sure.
There is a cafe on site, but bring snacks if you're trying to save money.
Olana (Hudson)
Address: 5720 NY-9G, Hudson, NY 12534 Phone: (518) 751-0344 Website: olana.org
This artist's house looks like something from a fairytale. Persian architecture in upstate New York... not something you would expect, but so beautiful.
The tours are interesting if want to learn more about it. If not, just walk the grounds. It's free and the Hudson River views are killer.
Pro tip: it gets crowded on nice weekends, so plan accordingly.
Incredible Places to Eat and Drink
City Winery Hudson Valley (Montgomery)
Address: 23 Factory St, Montgomery, NY 12549
Phone: (845) 424-0222
Website: citywinery.com/hudson-valley
The wine plus the setting? A total win-win.
It's in this old factory building and they have live music most weekends. The food is wonderful too.
Try to get a reservation if you're planning on going!
Lil' Deb's Oasis (Hudson) - a Hudson Valley icon
Address: 747 Columbia St, Hudson, NY 12534
Phone: (518) 828-4307 Website: lildebsoasis.com
This place is totally unique.
Tropical food in upstate New York with décor that's basically a fever dream. But you know what? The food is really good.
It's loud and colorful and a one-of-a-kind type of place, which I absolutely love.
Get the plantains. Trust me.
If You Want to See a Show
Hudson Valley Shakespeare Festival (Garrison)
Address: 2015 US-9, Garrison, NY 10524
Phone: (845) 265-9575
Website: hvshakespeare.org
Outdoor Shakespeare with the Hudson River behind the stage.
It's pretty magical. Even if you don't love Shakespeare, the setting makes it worth it.
Pro tip: bring layers - it gets cold when the sun goes down.
Hudson Hall (Hudson)
Address: 327 Warren St, Hudson, NY 12534
Phone: (518) 822-1438
Website: hudsonhall.org
Good venue for concerts and art shows. The building itself is beautiful - old opera house that they restored.
Check their calendar before you plan a trip!
Where to Stay
The Maker Hotel (Hudson)
Address: 302 Warren St, Hudson, NY 12534 Phone: (518) 509-2620 Website: themaker.com
Boutique hotel done right.
Each room is different and they put so much thought into the design. It's definitely worth the investment. Plus you can walk to most of the good restaurants in Hudson.
To note: the bar downstairs gets busy on weekends.
Inn at Silver Maple Farm (East Chatham)
Address: 1871 NY-295, East Chatham, NY 12060
Phone: (518) 781-3600
Website: silvermaplefarm.com
If you want quiet and cozy, this is it.
It's out in the middle of nowhere which is perfect for a digital detox getaway. If you're looking to spend an unplugged weekend, you can't beat this place.
The Family Stuff (If You Have Kids)
LEGOLAND New York (Goshen) - a must do thing in the Hudson Valley for kids 10 and under
Address: 1 LEGOLAND Blvd, Goshen, NY 10924 Phone: (845) 410-0290 Website: legoland.com/new-york
People are obsessed... and I get it.
It's basically Disney for LEGO fans. If your kids are into LEGOs, they'll absolutely love it here.
Pro tip: Buy tickets online - they are usually less expensive and you can skip the line.
Castle Fun Center (Chester)
Address: 109 Brookside Ave, Chester, NY 10918
Phone: (845) 469-2116
Website: thecastlefuncenter.com
Classic family fun center. Go-karts, mini golf, laser tag.
Kids love it. Great for rainy days when you need something fun to do inside. They have great pizza too!
Catskill Animal Sanctuary (Saugerties) - a perfect Hudson Valley activity for the animal lover
Address: 316 Old Stage Rd, Saugerties, NY 12477
Phone: (845) 336-8447
Website: casanctuary.org
Rescued farm animals living their best life.
The tours are sweet and educational. Kids get to meet pigs, cows, goats - all with names and personalities.
For info on our favorite Catskills wedding venues, check out this post!
Hudson River Maritime Museum (Kingston)
Address: 50 Rondout Landing, Kingston, NY 12401
Phone: (845) 338-0071
Website: hrmm.org
Famous for boats and river history.
If your kid is into either of those things, this is a can't miss. They occasionally have boat rides as well, which is another highlight.
Kingston's waterfront area is nice for walking around after.
Seasonal Real Talk
Fall: Yes, the foliage is gorgeous. It's also crowded which can make lodging more expensive. Go mid-week if possible.
Winter: Honestly pretty quiet. Good for cozy getaways but a lot of outdoor stuff closes.
Spring: My favorite time. Everything's blooming, weather's nice, no crowds yet.
Summer: Hot and busy but lots of festivals. Lake George Music Festival is actually great if you like music.
Here's What I'd Do in the Hudson Valley
If you're planning a romantic weekend, stay in Hudson. Walk Warren Street, eat at Lil' Deb's, see something at Hudson Hall.
Day trip to Storm King if weather's nice. Skip it if it's raining.
For families, LEGOLAND if your kids are the right age. Otherwise, do the Walkway and maybe the animal sanctuary.
Honestly? Don't try to do too much. Pick a few things and really enjoy them.
Ready to Plan Something Amazing?
I love talking about the Hudson Valley. But if you're planning something really special - like an engagement weekend or looking for wedding venues up here - you might want some professional help.
I work as a Hudson Valley wedding planner and I know this area inside and out. The Instagram-famous spots, the hidden gems, the places that look great in photos but are not great for events.
Want to create something unforgettable in the Hudson Valley? Let's chat about making it happen right.
Contact us and let's plan your perfect Hudson Valley experience.
For all the Hudson Valley wedding details, read our guide to weddings in Hudson Valley and the inside scoop on Hudson Valley New York wedding venues.
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