15 Unforgetable Things To Do In Middletown, NY

Before the strip malls and breweries, Middletown was a railroad boomtown. Founded in the early 1800s and officially incorporated in 1888, this Orange County city owes its rise to the Erie Railroad, which turned a sleepy farming village into a thriving industrial hub. At its peak, Middletown was a manufacturing powerhouse and a cultural crossroad, drawing immigrants, inventors, and outliers looking to build something permanent.

Its name came from its location—a “middle town” between other colonial settlements—and while that might sound uninspired, don’t let it fool you. Middletown has always punched above its weight. It’s the hometown of Ed and Lou Banach, Olympic gold medal wrestlers. It’s where the voice of Bugs Bunny, Mel Blanc, once performed on stage at the Paramount. And it’s where Orange County’s blue-collar roots meet a growing creative energy that you can feel in its theaters, trails, and taprooms.

So if you're looking for things to do in Middletown NY, you're not just filling an itinerary. You're stepping into a place with roots, resilience, and stories worth hearing. Here’s how to explore the best of it, one local-favorite stop at a time.

1. Catch a Movie at Fair Oaks Drive-In Theatre

Location: 365 Bloomingburg Rd, Middletown, NY 10940

The Fair Oaks Drive‑In, opened in May 1970, is one of the region’s enduring retro gems. Initially a single-screen outdoor theater, it closed in 1981 before being revived by Ronald Mege in 1990. Mege not only rebuilt the projection system but also added a second screen, transforming it into a popular double-screen venue for summer blockbusters.

Today, it seats up to 800 cars across two screens and operates seasonally from May through September. It offers modern amenities like localized FM audio (channels 103.9 & 91.9), accepts credit cards, and even allows pets—making it an accessible and memorable night out.

Starting in the 1970 debut showing of "Johnny Cash! The Man, His World, His Music" and "The Trouble With Girls" featuring Elvis Presley, Fair Oaks has entertained generations of movie lovers under the stars . After challenges in 2014, including ownership changes and legal setbacks, it reopened in 2015 and continues to bring nostalgic fun to families year after year

2. Explore the Galleria at Crystal Run

Location: 1 Galleria Dr, Middletown, NY 10941

Located just east of Middletown in Wallkill, the Galleria at Crystal Run debuted on April 1, 1992. Developed by The Pyramid Companies, it spans an impressive 1.1 million square feet over two floors and remains the second-largest mall in the Hudson Valley.

The Galleria was conceived as an update and replacement for the older Orange Plaza, anchored initially by retail names like G. Fox, Filene’s, JCPenney, Sears, and Steinbach, with a movie theater and more on site. Today, it houses around 120 diverse shops and restaurants, along with major anchors such as Macy’s, JCPenney, Target, and Dick’s Sporting Goods. Entertainment options have expanded to include a 16‑screen AMC theater, Urban Air Adventure Park, Round 1 Bowling & Amusement, Billy Beez play zone, and several dining venues from sushi to Mediterranean fare.

Over the decades, the mall has evolved with periodic renovations—like a significant 2015 aesthetic refresh using polished porcelain tile—to stay current and vibrant for local shoppers. It's both a shopping anchor for Middletown and a touchstone of 1990s and 2000s mall culture

3. Walk the Trails at Highland Lakes State Park

Location: Off Tamms Road, Middletown, NY 10940

Highland Lakes State Park is one of Orange County’s most expansive natural spaces, covering nearly 3,000 acres of woodlands, wetlands, and meadows. Located just a short drive from Middletown, it offers a rugged, undeveloped experience for those looking to reconnect with nature. Unlike more manicured parks, Highland Lakes features unmarked, multi-use trails perfect for hiking, horseback riding, and mountain biking, as well as ample opportunities for wildlife observation and photography.

The land was acquired by the state in the 1960s and remains intentionally wild—there are no paved paths or visitor centers here. This simplicity is part of its charm, offering peace, solitude, and a chance to see the region’s natural ecosystems in their raw form. Birdwatchers and botanists especially appreciate the variety of species that call the park home, from migratory warblers to native wildflowers.

4. Visit the Paramount Theatre

Location: 17 South St, Middletown, NY 10940

Standing proudly in the heart of downtown Middletown, the Paramount Theatre is both a historic landmark and a beacon of cultural life in the region. Opened in 1930 as part of the Paramount Pictures theater chain, this elegant venue was designed during the golden age of cinema, complete with grand Art Deco details, ornamental plasterwork, and a majestic auditorium that once hosted vaudeville acts, orchestras, and film premieres.

Though it closed in the 1970s, the theatre was saved from decline thanks to local efforts and city ownership, undergoing extensive restoration to recapture its original splendor. Today, it serves as a performing arts center that hosts a variety of events—from Broadway-style productions and film screenings to concerts, comedy shows, and community gatherings.

5. Grab Craft Beer at Clemson Bros. Brewery

Location: 22 Cottage St, Middletown, NY 10940

Housed in a beautifully restored 19th-century industrial building, Clemson Bros. Brewery blends Middletown’s industrial past with its rising craft beer scene. Once part of the Clemson Brothers hacksaw factory—a company founded in the late 1800s that helped define the city’s manufacturing era—the structure now buzzes with a completely different kind of energy: small-batch brews, live music, and a gastropub-style menu that makes it a favorite local hangout.

Inside, the brewery showcases exposed brick walls, high ceilings, and vintage factory equipment that nod to its heritage. Outside, a large patio offers space to enjoy a beer flight or burger under the stars. Signature beers like the Clemson Pilsner or Iron Horse IPA often rotate with seasonal specials, and everything is brewed onsite using traditional methods.

6. Check Out the Middletown Reservoir Trails

Location: 435 Van Duzer Rd, Middletown, NY 10940

A peaceful nature retreat tucked into the city's edge, the Middletown Reservoir Trails offer locals and visitors access to one of the most scenic and well-kept outdoor areas in the region. Once part of Middletown’s water supply system, the site has been carefully redeveloped into a public recreation space featuring over six miles of soft-surface trails that wind around the reservoirs and through wooded landscapes.

Open to walkers, runners, bikers, and leashed dogs, the trail system includes a mix of flat and gently sloping paths suitable for all fitness levels. Along the way, you'll pass tranquil water views, footbridges, and forested pockets that light up with color during fall foliage season.

7. Attend the Orange County Fair (July)

Location: 239 Wisner Ave, Middletown, NY 10940

For over 180 years, the Orange County Fair has been a summertime staple in Middletown, drawing visitors from across the Hudson Valley with its blend of tradition, thrills, and family-friendly fun. Established in 1841, it is one of New York State’s longest-running county fairs—and though it has evolved with the times, it still captures the charm of small-town Americana.

Held every July at the fairgrounds on Wisner Avenue, the event features classic attractions like livestock shows, 4-H exhibits, and agricultural displays, alongside modern entertainment such as demolition derbies, motorcycle stunt shows, and nightly concerts. A sprawling midway offers carnival rides, games, and all the deep-fried food your heart desires—from funnel cakes to giant turkey legs.

8. Visit the Harness Racing Museum (in nearby Goshen)

Location: 240 Main St, Goshen, NY 10924

Just a short drive from Middletown in the village of Goshen, the Harness Racing Museum & Hall of Fame offers a fascinating look into one of America’s oldest and most unique sports. Located in a beautifully preserved 1913 stable building alongside the historic Goshen Historic Track, the museum chronicles the evolution of harness racing—where horses race at a trot while pulling a driver in a two-wheeled cart called a sulky.

The Goshen track itself has been in operation since 1838, making it the oldest active harness racing track in the United States. Inside the museum, interactive exhibits, vintage racing memorabilia, art, and even a 3D simulator bring the sport to life. It’s a hit with both casual visitors and history buffs, offering something for all ages, including hands-on displays for kids.

9. Eat Pizza at Tony Boffa’s

Location: 51 Railroad Ave, Middletown, NY 10940

Few places in Middletown carry as much culinary legacy as Tony Boffa’s Restaurant. Family-owned and operated since 1951, this classic Italian-American eatery has been serving up red-sauce comfort food and some of the region’s most beloved pizza for over 70 years. It’s more than a place to eat—it’s a local institution where generations of families have gathered for birthdays, Sunday dinners, and post-game celebrations.

Located on Railroad Avenue, Tony Boffa’s blends old-school warmth with timeless flavors. Their thin-crust pizza, baked to a golden crisp and cut into square slices, is legendary among locals. Beyond the pies, the menu includes homemade meatballs, baked ziti, chicken parm, and other traditional dishes served in hearty portions.

10. See a Show at SUNY Orange’s William and Helen Richards Theatre

Location: Orange Hall, 24 Grandview Ave, Middletown, NY 10940

Tucked within the historic buildings of SUNY Orange’s Middletown campus, the William and Helen Richards Theatre at Orange Hall serves as the college’s cultural centerpiece. Named in honor of two longtime supporters of the arts and education, the theater hosts a variety of performances throughout the year, including student plays, concerts, guest lectures, and community events.

The venue itself is intimate and inviting, with seating for just over 350 and acoustics that make every performance feel close and immersive. While it’s primarily a space for SUNY Orange’s highly regarded arts and music programs, the theater also welcomes touring artists, regional theater companies, and local talent—making it a vital part of Middletown’s performing arts scene.

Set against the backdrop of a campus rich in history—the college was established in 1950 and occupies the grounds of the former Morrison Estate—the theater contributes to a deeper appreciation for the arts in an academic setting. It’s an ideal place to catch a show in a quieter, more personal atmosphere than a large venue, all while supporting the next generation of artists.

11. Go Apple Picking at Soons Orchards (Seasonal)

Location: 23 Soons Cir, New Hampton, NY 10958

Nothing says Hudson Valley autumn like apple picking, and Soons Orchards in nearby New Hampton is one of the best spots to enjoy this seasonal rite of passage. A family-run farm since 1910, Soons offers more than 30 varieties of apples across its scenic orchards, from crisp Honeycrisp and tart McIntosh to heirloom varieties you won’t find in supermarkets.

Open for U-pick on select weekends in September and October, the experience is as wholesome as it is fun. Visitors are welcomed with wagon rides to the orchards, sweeping views of the countryside, and the comforting scent of fresh apple cider in the air. The farm store, open year-round, sells homemade pies, cider donuts, jams, and local produce, making it hard to leave empty-handed.

12. Sip Wine at Clearview Vineyard

Location: 35 Clearview Ln, Warwick, NY 10990

Perched on a hillside just outside Middletown, Clearview Vineyard offers award-winning wines with a panoramic view to match. Established in 2007 by Frank and Karen Graessle, the vineyard has steadily grown into one of Orange County’s premier wine destinations. Its name reflects the serene setting—on a clear day, the distant peaks of the Shawangunk Mountains stretch across the horizon.

Open seasonally from spring through fall, Clearview’s tasting room is warm and welcoming, often featuring live acoustic music on weekends. Guests can sample a range of handcrafted wines, from crisp whites to robust reds, all made from estate-grown grapes. Standouts include their Cabernet Franc, Traminette, and a dessert-style Frontenac that locals rave about.

The setting is as much a part of the experience as the wine itself. Tables are spread across a lawn and patio, offering relaxed views of the vines and countryside. It’s a perfect spot for a laid-back afternoon date, a girls’ outing, or simply some solo time with a glass and a breeze.

3. Hike at Goosepond Mountain State Park

Location: Route 17M, Chester, NY 10918

Nestled in the Town of Chester, just west of Middletown, Goosepond Mountain State Park preserves approximately 1,558 acres of undeveloped woodlands, wetlands, and fields. Established in the early 1960s, this natural sanctuary was created using state bond act funds and remains intentionally raw and largely unmanicured.

The park is especially popular with hikers, birdwatchers, and horseback riders. Its network of unpaved trails weaves through varied terrain, including dense forest, marshy stretches, and serene meadows. A boardwalk allows access to otherwise inaccessible wet areas, offering an immersive glimpse into the park’s biodiversity.

The area also includes five acres of man-made wetlands, constructed to compensate for lost natural wetlands during nearby highway development.

14. Get Coffee at Something Sweet Café

Location: 17 North St, Middletown, NY 10940

What began in 2004 as Something Sweet Dessert Cafe, founded by pastry chef Anna Madden and her husband Dave, has since transformed into a refined Italian dining destination under a new name. Originally cherished for its scratch-made desserts and comforting café fare, the couple responded to changing times and a revitalizing downtown by reimagining their space into something wholly new.

After nearly 18 years, the café closed in April 2022. That spring marked the bittersweet end of a beloved local spot that launched the community’s Run 4 Downtown event and continued to serve up pastries and cozy meals in Middletown’s heart.

Reopening in May 2022 as Piccolo Cucina e Vino, the venue embraced a fresh concept: small plates, freshly made pasta and mozzarella, Italian-inspired sandwiches, and a curated wine and beer selection. Set within the same 1888-built building at 17 North Street, the redesign includes a solarium with glass walls overlooking the Downtown Park and a copper bar seating area that invites leisurely sips and conversation.

Although it’s no longer a coffee shop per se, Piccolo honors its roots as a place built on craftsmanship, comfort, and connection—now elevated through Italian flavors and an artful, intimate ambiance.

15. Take a Self-Guided Historic Walking Tour

Location: Start at Middletown Historical Society, 25 East Ave, Middletown, NY 10940

Middletown’s history lives in its architecture, and one of the best ways to experience it is with a self-guided walking tour through its downtown and surrounding neighborhoods. With roots stretching back to the early 18th century, the city has preserved a rich blend of Victorian homes, early 20th-century storefronts, and landmarks tied to its rise as a rail and manufacturing hub.

Maps for the tour are available through the Middletown Historical Society or City Hall, highlighting key sites like the 1896 Thrall Library building, the Victorian Gothic-style First Congregational Church, and residential streets lined with ornate, century-old homes. You’ll pass through areas shaped by the city’s booming railroad era, its industrial golden age, and its cultural evolution into a regional hub.

Along the way, stop into local coffee shops, antique stores, or grab a bite from one of the many family-run restaurants that dot the route. It’s a leisurely way to explore the city’s character and appreciate the craftsmanship of a bygone era.

Conclusion

Middletown doesn’t care if it looks good on Instagram. It’s not trying to be Hudson, Beacon, or New Paltz. It’s more working hands than wine spritzers, more demolition derby than designer denim. And that’s exactly why people keep coming back.

What you get here isn’t just a checklist of things to do in Middletown NY. You get stories. Like a century-old orchard still run by the same family. A brewery built inside a knife factory. A drive-in that still plays double features like it’s 1975. A theater where kids from SUNY Orange pour their guts into plays for crowds of fifty.

Middletown has always been in the middle of something. In the past, it was trains and tobacco. Today, it’s revival and reinvention. So if you’re tired of perfectly polished towns that feel more like movie sets than places people actually live, come here instead. Spend your money at a diner. Hike a trail with no name. Sit in the back row at the Paramount and listen for echoes.

Because Middletown may not be perfect, but it’s got a pulse—and that’s more than enough.

Interactive Map

Where to Eat in Middletown

Middletown vs Other NY cities

How to Get to Middletown

By Car

• From New York City: Take I-87 North (New York State Thruway) to Exit 16 (Harriman), then follow Route 17 West to Exit 120 or 120E for Middletown.
  ⏱️ Travel time: ~1 hr 20 min (70 miles).
• From Albany: Take I-87 South to Exit 17 (Newburgh), then I-84 West to Middletown.
  ⏱️ Travel time: ~1 hr 30 min (95 miles).
• From Scranton, PA: Take I-84 East directly into Middletown.
  ⏱️ Travel time: ~1 hr 10 min (70 miles).

By Train

• Take NJ Transit’s Port Jervis Line from Penn Station (NYC) or Secaucus Junction.
• Get off at Middletown-Town of Wallkill Station (just outside Middletown).
  ⏱️ Travel time: ~2 hours from NYC.

By Bus

• Short Line/Coach USA runs regular buses from NYC’s Port Authority Bus Terminal to Middletown.
• Stops include Crystal Run Mall and downtown Middletown.
  ⏱️ Travel time: ~1 hr 45 min.

By Air

• Stewart International Airport (SWF) in Newburgh is the closest airport (25 miles east).
• From there, take a taxi, rental car, or local shuttle.
• Major NYC airports (JFK, LaGuardia, Newark) are also options, followed by train or bus.

FAQ

1. What’s the general vibe of Middletown? Is it family-friendly?

Middletown has a mixed reputation: some see it as gritty or struggling, but many residents say it’s affordable, diverse, and practical. Families like the community feel, proximity to NYC (commuter rail), and ongoing downtown revitalization. It’s not as polished as nearby Warwick or Goshen, but it’s functional and livable.

2. Any favorite spots or restaurant recommendations?

Locals consistently recommend:

• Oak & Reed → upscale, seasonal American.
• Piccolo Cucina e Vino → authentic Italian.
• Equilibrium Brewery → craft beer & taproom.
• Players Restaurant & Lounge → casual American with nightlife.
  There’s also a growing café and bakery scene downtown.

3. Is housing and rent affordable? Any areas to avoid?

Housing in Middletown is more affordable than much of the Hudson Valley. Median home values are around $270K–$280K. Rent for a 1BR is ~$1,500/month.

• Safer, desirable areas: near SUNY Orange, Presidential Heights, East Main St. corridor.
• Areas needing caution: some South Street and Wickham Ave. blocks, where crime and blight are reported higher.

4. Is Middletown worth visiting?

Yes, Middletown is absolutely worth a visit, especially if you enjoy small cities that balance history, culture, and modern convenience. Many travelers are surprised at how much there is to see and do here compared to nearby towns. The Paramount Theatre alone is worth the trip—it’s a historic Art Deco landmark that still hosts concerts, comedy shows, and classic films. Beyond that, Middletown has a vibrant dining scene with local breweries and family-run restaurants, as well as nearby natural escapes like Highland Lakes State Park. Whether you’re a history buff, a foodie, or just passing through Orange County, Middletown offers more than meets the eye.

5. How do I spend a day in Middletown?

A full day in Middletown can be a mix of history, food, and outdoor exploration. Start with a coffee downtown before heading to the Harness Racing Museum & Hall of Fame in nearby Goshen, which tells the story of one of America’s oldest sports. In the afternoon, stroll the Orange County Arboretum, where beautifully maintained gardens and walking paths make for a peaceful escape. For families, LEGOLAND New York Resort is just a short drive away. End your day with dinner at Clemson Bros. Brewery or one of the city’s diverse restaurants, followed by a show or movie at the Paramount Theatre for a perfect wrap-up.

6. What is Middletown’s top tourist attraction?

The Paramount Theatre is often considered Middletown’s crown jewel and its most recognized attraction. Built in 1930, this Art Deco landmark has been beautifully restored and continues to host live performances, comedy acts, and classic films that bring the community together. The theatre has a nostalgic charm—you feel like you’re stepping back in time as soon as you enter. Its history of attracting both local audiences and notable performers makes it a must-see when in town. Visitors also appreciate its location, surrounded by downtown shops and eateries, making it easy to pair a show with dinner or a night out.

7. Is Middletown walkable?

Yes, Middletown is surprisingly walkable for a city its size. Downtown Middletown is compact, with many attractions, restaurants, and shops located within a few blocks. You can easily walk from the Paramount Theatre to the city’s cafés, boutiques, and even some historical spots. Residential neighborhoods such as Mechanicstown and Washington Heights are also accessible by foot, though they’re better suited for longer walks rather than quick errands. The city has invested in improving sidewalks and public spaces, making it easier for both residents and visitors to explore on foot. That said, for exploring the wider region, a car is still recommended.

8. Are there family-friendly activities in Middletown?

Absolutely! Middletown offers a wide range of family-friendly activities. LEGOLAND New York Resort is one of the most popular, drawing families from across the state for a full day of rides, shows, and themed attractions. But you don’t have to spend big to keep kids entertained—local parks like Fancher-Davidge Park and Highland Lakes State Park are perfect for picnics, hiking, or fishing. The Orange County Fairgrounds also hosts seasonal events that families love, including the annual fair in summer.