LOVE sign and vintage car with other eclectic decorations at Four Brothers Drive-In Theater in Amenia, Hudson Valley, New York via Mad Hatters NYC Blog

Hotel Caravana at Four Brothers Drive-In: Retro Heaven in the Hudson Valley

We love New York City. But we also love a good getaway. Especially when the weather warms up and tourists descend on the city en masse. Unfortunately, circumstances–often a lack of time, money, or transportation–prevent a holiday to the exotic destination of our dreams. Luckily, there are innumerable locales to explore in the tri-state area. Even better, there are tremendous options in the state of New York itself. And it just so happens we recently stumbled upon a new destination for the perfect getaway that is less than two hours from Manhattan: Hotel Caravana at the Four Brothers Drive-in Theatre in Amenia, New York.

What is Hotel Caravana?

Exterior shot of Hotel Caravana Airstream including private deck and vintage bicycles via Mad Hatters NYC Blog

Anchored by the 40-year-old outpost of Four Brothers Pizza Inn and located on the grounds of the Four Brothers Drive-in Theatre, Hotel Caravana is the newest venture of the namesake Stefanopoulos brothers. It’s a fully renovated, quirkily decorated, silver aluminum 1967 Airstream trailer, with a sizable deck attached. Hotel Caravana is available for rental on weekends throughout the drive-in season. It sleeps 4-6 guests (though we don’t recommend more than 4 adults) and offers a kitchenette and a bathroom with a stand up shower. You won’t be roughing it here, the refurbished Airstream offers creature comforts like heat and A/C, WiFi, and an interior and exterior sound system. Additional amenities include private parking, a minibar stocked with a selection of snacks and refreshments, and room service from 3:00 pm-9:30 pm.

Pet sheep named Becky at Four Brothers Drive-In Theater in Amenia, Hudson Valley, New York via Mad Hatters NYC Blog
Becky with the good fleece 😉

Want to step outside your temporary tiny home? Your private deck is equipped with ample seating and a hammock so you can enjoy the lush surroundings. There’s a nearby fire pit with swing chairs and lawn games to keep you fully entertained on the grounds of the Four Brothers Drive-In Theatre. (There’s also a resident pet sheep named Becky, who is affectionate but loves to head-butt.) If you’re feeling particularly adventurous, there are four vintage bikes provided so you can discover the surrounding area.

Where is Hotel Caravana located?

Sign reading Welcome to Our World at Four Brothers Drive-In Theater in Amenia, Hudson Valley, New York via Mad Hatters NYC Blog

Hotel Caravana is located in the charming, bucolic town of Amenia in Dutchess County, New York. More than 50 years ago, it was a popular summer destination, known for several summer camps and family-friendly vacation cottages along what was then Lake Amenia. But then the dam broke, the lake became wetlands, and the town withered for the next few decades. It wasn’t until the introduction of the Metro-North Harlem Line station in Wassaic back in 2000 that the town’s fortunes began to change. For decades, Four Brothers Pizza Inn’s outpost in the town center was the focal point of dining in the community, and it is still a mainstay to this very day. The introduction of an adjacent drive-in theatre in 2013 added an entertainment space for the community, which the community has since embraced.

Cute bathroom stalls at Four Brothers Drive-In Theater in Amenia, Hudson Valley, New York via Mad Hatters NYC Blog
Even the bathrooms are adorable!

Four Brothers Drive-In Theatre captures the spirit and nostalgia of the traditional drive-in you might remember from movie classics like American Graffiti. But it isn’t a remnant from that era. Four Brothers Drive-In Theatre is a reimagined version for today’s entertainment junkie. As soon as you enter (which you can do as early as 11:00 am when the Grand Shack opens), you’ll notice an assortment of custom-made signs and furniture to welcome you into the space. There’s an Art Deco painting by beloved local artist Peter Wing. You can order your food online with car hop delivery, and you can get your windshield cleaned or battery jumped if needed. Service is central here, and your comfort is always top of mind.

When can I stay at Hotel Caravana?

Hotel Caravana is available for booking every weekend during the drive-in’s seasonal run from March through November. A double feature is on tap each night, the first of which starts around 8:00 pm. Hotel check in is at 3:00 pm and check out is by 11:00 am the following morning.

Looking for more weekend getaways from New York City? Check out these things to do in North Fork, Long Island.

How do I get to Hotel Caravana?

Rotary phone and welcome sign at Hotel Caravana at Four Brothers Drive-In Theater in Amenia, Hudson Valley, New York via Mad Hatters NYC Blog
Use the rotary phone to call for room service

There are two ways to visit Hotel Caravana: by car and by train. To reach Amenia by car, we recommend taking the Taconic State Parkway, a scenic road through the eastern Hudson River Valley. It has breathtaking treelines, particularly lovely during the spring and fall, quaint stone overpasses, and multiple lookout points along the route. If you’re an electric vehicle driver, thank you for reducing your carbon footprint! But also note that Hotel Caravana has an electric vehicle charger conveniently located on site. (It’s the only outdoor theatre in the country to offer this.) To reach Amenia by train, take the Metro-North Harlem Line to the Wassaic Station. From there, a cab can be arranged with the helpful staff of Hotel Caravana to coordinate the five minute drive to your accommodations.

Why should I visit Hotel Caravana?

Hotel Caravana outdoor deck at night via Mad Hatters NYC Blog
Margherita Pizza with a Grecian Twist at

Your adventure doesn’t begin when the first movie starts, it begins the moment you check in to Hotel Caravana. There are a number of fun things to do both in the immediate area and just a little further away. First and foremost, you can get a solid meal just footsteps away from your accommodations. Four Brothers Pizza Inn has been around for decades, and not by accident. Locals love their excellent Greek salads and tasty pizzas. Their signature pizzas, with a decidedly “Grecian” touch, have a higher edge to their crust than, say, a traditional New York-style pie. But we can assure you, they are excellent. (Leftover pizza is a great movie snack!)

 
 
 
 
 
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Once you’ve refueled, don’t forget that you have four vintage bikes at your disposal. Take a ride around the quaint town center. Or if you’re looking for something a little more challenging, we suggest strolling the natural splendor of the nearby Harlem Valley Rail Trail, which has 15 paved miles running through stunning rural Dutchess and Columbia County landscapes. Or maybe you like your nature paired with a glass of red or white. Then opt instead for a 13 minute drive or taxi ride to Millbrook Vineyards & Winery. Hudson Valley’s flagship winery offers tours, tastings, and a vineyard walking trail. Whichever you choose, you’ll have plenty to keep you occupied leading up to showtime.

Everybody needs a break from time to time. The next time you’re desperate for a short getaway, try something different. Consider absconding to Hotel Caravana in Amenia, where you’ll find a unique and yet familiar upstate New York experience. Book now!

Disclosure: We received a complimentary stay at Hotel Caravana so we could share our experience with our readers. As always, the opinions are entirely our own.

– L. & J.

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Trudy
Guest

Your trip sounds amazing and I love all the green scenery. I haven’t been to a drive-in and I think that is the part I would enjoy most.

Tara
Guest

Drive In Theater- enough said!
But then there was a picture of their deck and the rotary phone.
I love that they have bikes to ride around. What a fun find.

Cynthia | Adventuring Woman
Guest

This is so cute! I stayed in a tiny trailer once in Savannah, this one is luxe. And that pizza looks to die for. Quite dangerous having delicious pizza just footsteps away. For my waistline, and for them, as I might never leave! Since I can also see movies at the drive-in. What more is needed? 🙂

Kara DiDomizio
Guest

What an absolutely perfect getaway! It looks like such an absolutely fun place to visit and it looks lovely. The bathrooms, like you said, look so cute too and the Four Brothers pizza looks so delicious!

That is awesome about the bike rentals to take advantage of as well. Great post guys! I would love to visit here.

Tip and Jam
Guest

Once again, you guys have found a NY gem! I could taste the fresh upstate spring air in your post. And, once again, you’ve made us miss Manhattan and the area. JAM and I went to a drive in on our first date way back in a different millennium. So this post gave us a hit of nostalgia. Speaking of JAM, she is having her second major surgery since January and she has been on the DL, but we should be back to posting by July and hopefully return to NYC for a visit. Maybe we could hit up McSorley’s… Read more »

Chris
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Chris

This looks really fun! Great getaway from the busy hustle and bustle of daily life. Do they show new films or classics too?