Middletown Explore Local With RVshare

Incorporated back in 1888 and the site of major events like the Orange County Fair, Middletown is a unique New York community teeming with great to-do options. Here are some of our favorite places to explore in town!

*Note: Some of the suggestions may not be doable due to coronavirus closures, but keep this list handy for when things start opening back up more! Be sure to check individual pages for specific operation details.

Those who live in and around Middletown are lucky to be in close proximity to a wide array of wonderful state and national parks and recreation areas. Here are some of the coolest state parks in Middleton, NY.

Bear Mountain State Park

Along with the namesake peak itself, which rises more than 1,200 feet above sea level, Bear Mountain State Park is home to a wide variety of beautiful natural landscapes, including rugged mountain ranges as well as portions of the winding Hudson River. The park also offers many developed facilities to make your visit even more fun, including a swimming pool, seasonal outdoor skating rink, and even an on-site museum and zoo!

Clarence Fahnestock State Park

Originally set aside as a memorial to its namesake back in 1929, Clarence Fahnestock State Park continues to delight outdoor enthusiasts today with its more than 14,000 acres of recreational opportunities. Straddling Putnam and Dutchess counties, the park includes picnic areas, on-site camping, an outdoor education center and fishing, birding and hunting opportunities, as well as miles of trail perfect for both summer hiking and winter snowshoeing.

Harriman State Park

A sprawling wilderness encompassing more than 47,000 acres, including 31 bodies of water and more than 200 miles of hiking trails, Harriman State Park is the second largest in New York, and is a popular spot for locals and those from further afield both in the summer and winter. Whether it’s ice fishing and cross-country skiing or hiking, boating, and biking, there’s no shortage of things to see and do here. It’s all located less than an hour from downtown Middletown, which is to say: what are you waiting for?

Highland Lakes State Park

With more than 3,000 acres of undeveloped woods ripe for roaming, Highland Lakes State Park is a favorite among Middletown-area hikers, equestrians, and fisherfolk. The park is undeveloped, offering limited parking and no toilet facilities, so when you visit, be prepared for the great outdoors — seriously! 

Pochuck Mountain State Forest

Once considered an impenetrable swamp, known amongst early settlers as the “drowned lands,” today, Pochuck Mountain State Forest cuts a much friendlier profile — and is a common site for outdoor recreation and relaxation for New Yorkers from all over. Open year-round and fee-free, this wilderness is named after a peak that rises 1,194 feet above sea level, and whose name comes from the Lenape language, meaning “out of the way place.” You’ll certainly feel like you’ve gotten away from it all when you visit!

Schunemunk Mountain State Park

Covering more than 3,300 acres of rolling green hillsides and beautiful forested pathways, Schunemunk Mountain State Park contains eight marked hiking trails and is also popular among area hunters, who are particularly drawn by the area’s overabundant deer. Be sure to wear something bright when you’re tackling its 20+ miles of hiking trails, if you’re visiting during hunting season. You can never be too safe!

Sterling Forest State Park

A massive swath of New York countryside located close to the New Jersey state line, Sterling Forest State Park covers nearly 22,000 acres — and is shockingly untouched and wild, despite its proximity to densely populated urban areas. This preserved deep forest habitat is a haven for many plants and animals who can’t thrive elsewhere, including black bears, a wide variety of hawks, and a choir of different types of songbirds.

Wawayanda State Park (New Jersey)

Although it may technically be over state lines, Wawayanda State Park is less than 40 minutes outside of Middletown, making it a closer venture than many of the other parks named here. Plus, it’s got a lot to offer: more than 34,000 of beautiful countryside including 60 miles of hiking trails, 20 of which are along the famed Appalachian Trail!

There are plenty of fascinating places to get your boots on the ground in and around Middletown. Here are some of our favorite hiking trails in the area.

Cornish Estate Trail

Running just shy of two miles total and seeing only a few undulating hills, the Cornish Estate Trail is firmly in the easy hiking category — but still offers visitors an amazing chance to get up close and personal with a piece of living history. Showcasing the ruins of an ancient estate, this trail also offers river views and is partially paved for ease of use.

Tamms Pond, Highland Lake and Beaver Pond Loop

An easy, but lengthy, hiking trail tucked into Highland Lakes State Park, the Tamms Pond, Highland Lake and Beaver Pond Loop winds adventurers through almost six miles of beautiful countryside, including lakeside views and green forested areas, which are also frequented by horseback riders and mountain bikers. Seeing less than 500 feet in elevation gain along the way, this trail is perfect for someone looking for a hike that’s not strenuous, but which is long and leisurely enough to take a whole afternoon.

Stairway to Heaven Trail

An out-and-back trail running just shy of three miles and seeing a touch less than 1,000 feet in elevation gain along the way, the Stairway to Heaven Trail is moderately challenging, but a whole lot less intense than, say, a StairMaster… and the views are way better, too! Located in New Jersey’s Wawayanda State Park, this trail is renowned for its beautiful wildflowers and is dog-friendly, too. Its many large boulders also make it popular for area rock climbers, so be sure to keep an eye out (and up)!

Bear Mountain

If you’re headed to Bear Mountain State Park, you simply have to summit the namesake peak — especially since it’s no Kilimanjaro! At just shy of four miles round trip and seeing almost 1,200 feet of elevation gain along the way, the Bear Mountain hike is certainly not easy… but it’s by no means impossibly difficult, either. Keep in mind that, thanks to its panoramic views, this trail is quite popular and can easily fill up on the weekends, so if you want some space to yourself, go early… or on a Wednesday!

Breakneck Ridge, Notch, Brook Loop

At just over four miles altogether and seeing almost 1,500 feet in elevation gain along th way, the Breakneck Ridge, Notch, Brook Loop trail is certainly steep. But for those in the right kind of shape to tackle it, this hike is more than worth the effort, offering a climb through a beautiful forest setting followed by sweeping views of the river and valley below. Fido’s welcome, too, as long as he stays on-leash!

From scaling nearby mountains to exploring the neighborhood, there’s so much to see and do in Middletown… which is exactly why you’re gonna need some hearty meals! No matter what you’re craving, you can find what you’re looking for in town. Here are some options.

Tony Boffa’s

When you’re in this kind of proximity to New Jersey and New York City, seeking out the very best Italian restaurant is a bit of a feat — there’s just so much to choose from. But long-time Middletown residents are likely to place Tony Boffa’s near the top of the list, thanks to its classic atmosphere and even-more-classic menu. Each item is made with the freshest ingredients and three generations of family love. Buon appetito!

Asian 211 Bistro

Whether you’re looking for Chinese, Japanese, Thai food, or something else entirely, Asian 211 Bistro serves up the very best Asian cuisine in town — including sushi and sashimi for the most adventurous diners among us. Scoring consistent four- and five-star ratings among diners, this place has earned its reputation for quality and consistency.

Frontera Tacos & Tequila

Middletown is nowhere near the Mexican border… but that doesn’t mean you can’t enjoy some mean, authentic Mexican eats while you’re in town. Along with its namesake dishes and drinks, Frontera Tacos & Tequila serves up a wide array of other spicy, homemade treats — and given its status as a family restaurant run by brothers who hail from Mexico, you can rest assured that everything is authentic.

Saffron Fine Indian Cuisine

Offering spicy, satisfying meals fit to satisfy the entire family, including vegetarian and vegan options for the plant-based set, Saffron Fine Indian Cuisine is the Middletown go-to when you’re in the mood for Tandoori delights, curries, Biryani and more. Along with the food menu, enjoy a hand-crafted cocktail or local beer thanks to the restaurant’s full bar.

Mix N Mac Mac & Cheese

Even the most divided family can agree on one thing: mac and cheese is delicious. And at Middletown’s unique Mix N Mac cafe, you’ll find a plethora of everyone’s favorite on the menu: dozens of varieties of everyone’s favorite comfort food, including gluten free and vegan options. Choose from menu items or mix up your very own mac & cheese creation! 

Great dining and the great outdoors are, well, great — but they’re also just the beginning of your Middletown adventure. Here are our favorite things to do with the fam, your significant other, or simply by yourself this weekend (or whenever). 

For Kids and Families

Middletown is an incredible place to spend quality family time together. Here are some of our favorite options for kids of all ages.

Hit the Orchards

Middletown is lucky enough to be situated in a fruitful neck of the woods — literally. And who doesn’t love the satisfaction of being able to select their very own apples, right from the tree? Nearby farms like Apple Ridge Orchards and Masker Orchards make it possible to get your hands on your very own apples as soon as they ripen, while also offering other fun family activities like seasonal pumpkin patches, petting zoos, and more.

Go Bowling

A sport that’s accessible for the whole family (though the littlest ones might need bumpers for a while), bowling is a great way to spend active time together and can keep everyone entertained. Middletown’s local go-to is Quinnz Pinz, and also offers delicious food, drinks, and event hosting space along with its alleys.

At Night

You’re unlikely to run out of things to do in Middletown during the daytime, but what about after night falls? Here are some of the best after-hours options in this part of New York State.

Catch a Flick — Old-School Style

Movie night is one thing… but a trip to the drive-in? That’s a whole ‘nother kettle of fish. Middletown’s Fair Oaks Drive-In Theatre is the place to go when you want your film served with a side of nostalgia… not to mention delicious made-to-order food as well as traditional cinema snacks. All in the privacy of your very own vehicle!

Wine and Cider Tasting

While Middletown isn’t quite the Finger Lakes, New York State is still understandably proud of its fantastic wines — and going wine tasting is a great way to while away an evening. Middletown is also home to a variety of local cider mills, thanks to its proximity to apple orchards. Either way, this is one of our top picks for those looking for things for couples to do in Middletown!

Cheap Things to Do in Middletown

We get it: you want to enjoy yourself, but you don’t want to spend your kid’s college education. Here are our favorite low-cost options in Middletown.

Meander the Sculpture Garden

Technically located in the neighboring town of Warick, the Pacem in Terris Sculpture Garden is a unique outdoor art installation that feels like stepping into another world. Best of all, it’s free and open to the public to enter, though generous donations are accepted.

Zip on By

Looking for a whole new way to get familiar with the countryside? Consider flying along the tree tops with the birds and bees by braving a zipline! Mountain Creek Zip Tours is located just south of the border in one of the most scenic parts of New Jersey, and along with affordable ziplining tours offers all sorts of other adventures, too!

Free Things to Do in Middletown

It’s true: there’s tons of fun to be had absolutely free of charge!

Step Back in Time

Orange County, New York has been an important part of the country throughout history, and there are plenty of interesting, historically significant sites to visit that don’t cost a dime. To get started, check out the Orange County visitation bureau’s website to enjoy a self-guided “Revolutionary” tour that will introduce you to the Last Encampment of the Continental Army, the New Windsor Cantonment, and more.

Local Parks

In addition to the parks we mentioned above, there are many local parks with the Middletown area to check out! Grab the family for a nice picnic or leisurely walk.

Spas in Middletown

Everyone needs some plain old “me time” now and again. Whether it’s a relaxing massage or a new hairdo, here are the best day spas and salons for you to consider in Middletown, NY.

King Relaxation

Along with relaxation, massage therapy can offer a host of other benefits: improved circulation, better muscle function… it can even be beneficial to your digestion. Not to mention it simply feels good! King Relaxation is the Middletown go-to for bodywork in a wide range of modalities and also offers a dry sauna and hot towel treatment.

C’est La Vie Spa and Salon

Life can throw us some curveballs from time to time… but taking the time for self care can make a huge difference when it comes to weathering them. C’est La Vie Spa and Salon offers a full range of spa treatments, such as massages and facials, as well as beautifying services like hair cuts and color, manicures and pedicures, waxing, professional makeup and more. You’ll be sure to look as good as you feel when you leave!

Best Gyms & Yoga Studios

Staying in shape can do more than make you feel good in your skin… it can make you feel good in your soul. Here are the best gyms and yoga studios in Middletown, NY for those looking to get in a sweat session.

Ayo Fitness

The kind of comprehensive gym environment that has everything you need to meet your goals — including the stuff you didn’t even know you needed — Ayo Fitness is a local go-to for newbies and gym rats alike. From cardio equipment and free weights to dedicated strength training machines and fun and motivating group classes, it’s more than a gym: it’s a community and a lifestyle.

Happy Buddha Yoga

It’s worth the short drive to Goshen to engage in your practice at Happy Buddha Yoga, known for its low-key, community vibe that helps you find both strength and lightness on the mat. Choose from a wide range of classes and settle in for a challenging, yet relaxing workout led by an empathetic and experienced professional!

Middletown is anything but boring… but there are also some incredible day trips well worth taking in the area!

New York City

How lucky are Middletown residents to be able to get to New York City in as little as an hour and a half — which means you can easily bop into town for dinner and a show and be home in time to tuck the kids in? The best part about visiting New York City is not having to actually stay there once you’re with the hustle and bustle!

New Haven

Another cool thing about living in this part of the country is how easy it is to find yourself in a different state in a matter of mere hours. Check out New Haven, one of the happenin’-est places in Connecticut, known for its Ivy League status and wide range of cultural activities and exhibits. Museums, art galleries, and dining options abound!

As a final reminder, some of these activities may need to wait until businesses fully reopen from coronavirus closures. However, there is still much to see and experience in Middletown that you can enjoy today! What are your favorite spots in Middletown? Send them our way to [email protected] or by tagging us on Instagram @rvshare and using the hashtag #rvsharelocal.