48 Hours in Middletown

Park at 9-15 North Main Street, Middletown

Settled in the 1700’s, Middletown was named for its location halfway between the Hudson and Delaware Rivers. Today, it’s Orange County’s 2nd largest city, sitting at the crossroads of two interstate highways. A multitude of lodging, dining, and shopping options make it a popular stop for travelers, but there are many more things to see and do all year long. Victorian homes and buildings in the city display the prosperity that followed the Erie Railroad in 1843. Recent renovations are restoring the luster and attracting new tourist-friendly downtown businesses including two new breweries and a seasonal farmers’ market hosting family-friendly events. The well-known Orange County Fair, Orange County Fair Speedway, and the Route 211 “Miracle Mile” are in the Town of Wallkill surrounding the City of Middletown. Take a ride to explore the area, but stroll through the downtown to appreciate all of its unique character.

Friday evening
Take to the air and experience glorious views of the Orange County landscape from a hot air balloon! Between May and October, three different companies launch these lofty adventures from Randall Airport, usually at sunrise and 2-hours before sunset. Some even provide champagne! It’s not unusual to look up and see the colorful orbs high above the Middletown sky.

In summer months, bring your folding chairs and head to the heart of downtown for free weekly Friday night concerts at Festival Square. Several restaurants are just steps away including Zagat-rated, Nina, located in a vintage 1800 storefront at 27 West Main Street. It earned high praise for its inventive food and sophisticated ambiance. Time things right and you might even catch the concert from their outdoor patio.

Regardless of the season, stop by the historic Paramount Theatre at 17 South Street. With its Mighty Wurlitzer pipe organ, ornate ceilings, and elegant décor, this renovated landmark has retained all of its 1930’s splendor. The historic 1100-seat theatre is host to live performances and film, as well as the Hoboken International Film Festival held during the last week of May. Concerts, comedy shows, first run and classic films are regularly on the marquee. (). See what’s playing!

Relax overnight at the Courtyard by Marriott, or their sister property, Hampton Inn, on Crystal Run Road. Both are within close walking distance to popular bars and restaurants and just minutes by car from the Galleria Mall.

Take the self-guided International Tree Tour at the Middletown SUNY Orange campus for a glimpse into cultures and ecosystems from the far reaches of the globe. Stop by the Gallery at Orange Hall to catch ongoing exhibits, musical performances, demonstrations, and lectures held throughout the year. Get in the holiday spirit when the college’s ornate 40-room mansion, Morrison Hall, is splendidly decorated by the Middletown Garden Lovers Club and opened to the public on select December weekends.

Get outdoors! The 3,000 acres of undeveloped woods and lakes at Highland Lakes State Park are a good year-round bet for fishing, hiking, horseback riding, and flying model air planes, but check with the Palisades Interstate Park Commission for permit requirements before you go. Kids love to be outdoors, too, and the Tadpole Trail at Hunter Farm Preserve was created just for them. The ¾ mile trail has 7 activity stations for them to learn about the natural habitat, wildlife, and plants. The self-guided audio tour can be downloaded onto your MP3 player. Spiritual seekers are invited to roam 60-acres of grounds dotted with trails, shrines, and gardens at the National Carmelite Shrine, open to the public for meditation and relaxation.

When you’ve worked up an appetite, head downtown for a delicious lunch.  Called “Middletown’s best kept secret,” Something Sweet Dessert Café serves eclectic dishes made from scratch Monday through Saturday. The nearby landmark, Tony Boffa’s, earned its “Best Italian Restaurant” designation cooking up authentic family recipes since 1951. It’s open all weekend long. Clemson Bros. Brewery, located in a newly renovated 1897 hacksaw factory building, is the ideal place for craft beer aficionados to sample brews and nosh on pizzas, burgers, and salads.

Carnival fun and the excitement of an old-fashioned Demolition Derby come to the Orange County Fair during late July. Keep an eye out for the giant Ferris wheel! Catch the thrill of more serious racing action at the adjacent Orange County Fair Speedway weekends from spring right through to Eastern States Weekend in mid-October. The hard clay oval is said to be “the oldest continuously operating racing surface in the world.”

All year long, youngsters enjoy the indoor rides and games at The Party Zone USA every Friday through Sunday. Kiddie and toddler amusements are also the name of the game at Chuck E. Cheese‘s, and at the brand new Billy Beez play arena at the Galleria. Kids 10 and older have fun taking aim year round at the MSG Paintball Fields on Bart Bull Road. Walk-ins are welcome Saturdays and Sundays from 9-5. They even rent camo coveralls if you forget extra play clothes.

Saturday Night
Destefano’s Old Erie is a downtown neighborhood favorite. This lively restaurant has a menu full of comfort food and Italian dishes. It fills up quickly, so you may want to call ahead for a table. Stay late and you might catch some live music. Voted “Best BBQ and music combo throughout the Hudson Valley,” Brian’s Backyard BBQ on the outskirts of Middletown regularly features incredible live music from national, regional, and local acts. For a more sophisticated dining atmosphere, see what CIA Chef John Botti has prepared for you at John’s Harvest Inn. Admire the enormous clock collection at this long-standing establishment while you wait for your order to arrive.

Take a drive through Middletown’s scenic countryside and pick up some souvenirs at Pierson’s Farm, a seventh generation farm on Route 211 West. Peruse their neat gift shop filled with country decorations, homemade jams, candles, and their specialty, Angus beef. From late September through October their weekend hayrides, 3-acre corn maze, and pumpkin patch are delightfully fun. The kids will also love the inflatables and farm animals. Maples Farm & Garden Center on Route 17M is another fall hot spot with u-pick pumpkins, hayrides, a hay maze, and a country fair midway. Take in the aroma of fresh baked goods as you choose from the country crafts, cut flowers, and gardening items that fill their year-round farm store.

Don’t leave without a shopping excursion to the indoor weekend Middletown Flea Market on Dolson Avenue. You never know what you’ll find! More extravagant treasure hunters can score big at The Shanty Roost, a vintage and antique store on Goshen Turnpike. Their Facebook page promises a “unique rural shopping experience.” If there’s still room in the trunk, the wide selection of shops on Route 211 including the Galleria and Orange Plaza, are handy places to pick up anything else you might need before heading home.

Randall Airport Ballooning:
Above the Clouds. 845-692-2556, abovethecloudsinc.com
Fantasy Balloon Flights. 845-856-7103, fantasyfliers.com
Wandering Winds Hot Air Balloon Adventures. 845-754-8540, wanderingwindshotairballoons.com

Nina. 845-344-6800, www.nina-restaurant.com 
Historic Paramount Theatre.  845-346-4195, http://middletownparamount.com
Hoboken International Film Festival. 845-683-1535, www.hobokeninternationalfilmfestival.com
Courtyard Marriott. 845-695-0606, www.marriott.com/hotels/travel/swfcy-courtyard-middletown
Hampton Inn. 845-344-3400, www.hamptoninn3.hilton.com/en/hotels/new-york/hampton-inn-middletown-MLTNYHX/index.html
Galleria Mall.  845-692-8883, www.galleriacrystalrun.com 

International Tree Tour at SUNY Orange.   845-344-6222, http://www.sunyorange.edu/inttreetour/
Gallery at Orange Hall. 845-341-4891, www.sunyorange.edu/culturalaffairs
Highland Lakes State Park. 845-786-2701, http://parks.ny.gov/parks/5/details.aspx
Tadpole Trail at Hunter Farm Preserve. 845-469-0952, www.oclt.org
National Carmelite Shrine. 845-343-1879, www.ourladyofmtcarmelshrine.com
Something Sweet Dessert & Café. 845-343-2233, www.somethingsweetcafe.com
Tony Boffa’s Restaurant. 845-343-8842, www.tonyboffas.com
Clemson Brothers Brewery. 845-775-4638, www.clemsonbrewing.com
Orange County Fair. 845-343-4826, www.orangecountyfair.com
Orange County Fair Speedway.  845-342-2573, www.orangecountyfairspeedway.net
Party Zone USA.  866-983-4592, www.thepartyzoneusa.com
Chuck E. Cheese’s. 845-342-5781, www.chuckecheese.com/storedetails/ny/middletown/524
Billy Beez.  845-208-8326, http://billybeezus.com/location/galleria-at-crystal-run
MSG Paintball. 845-457-4678, http://www.msgpaintball.com
DeStefano’s Olde Erie. 845-344-3743, www.eriegrille.com
Brian’s Backyard BBQ. 845-692-3227, www.briansbackyardbbq.com
John’s Harvest Inn.  845-343-6630, www.johnsharvestinn.com
Pierson’s Farm.  845-386-1882, www.piersonsfarm.com
Maples Farm & Garden Center. 845-344-0330, www.maplesfarm.com
Middletown Indoor Flea Market. 914-552-3995. www.middletownfleamarket.com
The Shanty Roost. 845-820-1817, www.facebook.com/TheShantyRoost

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