Welcome to Highland Avenue — Middletown’s Hidden Culinary Gem
If you think Middletown, NY’s food scene is limited to the downtown or Dolson areas, think again! Nestled in the northeast corner, the Highland Avenue neighborhood offers one of the area’s most exciting (and underrated) collections of restaurants, bakeries, food trucks, and cafés. Here, local flavor meets global cuisine, and hidden gems sit right beside long-time favorite spots. Whether you’re a craving-driven local or a visitor eager to eat like an insider, Highland Avenue is packed with delicious discoveries.
The Main Drag: Where Highland Avenue Meets Taste
The stretch of Highland Avenue between Wickham Avenue and James P. Kelly Way is the heart of the neighborhood’s food scene. Here’s where the action (and aroma) is:
Highland Avenue Pizza & Grill (524 Highland Ave)
A cornerstone for neighborhood families and students alike, this classic pizzeria serves up much more than just a standard slice. The hand-tossed pies — try the chicken bacon ranch or classic margherita — are crowd-pleasers, but their menu stretches to include hearty heroes, spaghetti with homemade sauce, and a mean plate of zeppoles. Prices are easy on the wallet (most pies $15–$20), making it a favorite after-school or post-game stop.
Las Delicias Mexicanas (on Highland near North St Intersection)
A true local secret, this colorful storefront offers an authentic menu of tacos al pastor, tortas, tamales, and aguas frescas. Walk in for the heavenly aroma of fresh masa and sizzling carnitas. Everything is made in-house — especially the corn tortillas, which anchor every order. Prices hover in the $2–$10 range, making this a budget-friendly stop bursting with authentic flavor.
Highland Bagels & Café (corner of Highland Ave & Wickham Ave)
If it’s breakfast or coffee you’re after, Highland Bagels is the fuel station of choice. Known for plump, chewy bagels (baked daily) and friendly staff who remember your order, this café also whips up breakfast sandwiches, avocado toast, and locally roasted coffee drinks. The vibe is always warm and relaxed — perfect for a quick bite or a lingering morning.
Sweet Treats & Bakeries
Deli Delish & Bakery (618 Highland Ave)
One of Highland Avenue’s most beloved spots, Deli Delish pairs classic NY deli sandwiches with house-made sweets. The cookies, brownies, and signature carrot cake are always stocked at the counter, and locals swear by the lox bagel or the turkey BLT. Don’t miss their homemade fruit danishes on the weekend — they sell out fast! Most pastries and sandwiches are under $10, and their takeout options are great for picnics at nearby Fancher-Davidge Park.
El Pueblo Panadería (near Highland Ave & David St)
This under-the-radar bakery specializes in traditional Mexican pan dulce (sweet breads) — think conchas, orejas, and cream-filled empanadas. You can stop by for coffee and a pastry on a crisp morning, or grab a box to impress friends at your next gathering. Prices are unbeatable, with most treats well under $2 each.
Food Trucks & Street Eats
Tacos El Güero (usually parked near Highland Laundry, 712 Highland Ave)
On most afternoons, you’ll find a steady line at this food truck famous for its street tacos, roasted elote (corn on the cob), and icy paletas (popsicles) in summer. The truck’s birria tacos have developed a cult following — they’re juicy, rich, and cheesy, everything you want in true Jalisco-style fare. For less than $10, you can eat like royalty.
Maddy’s Latin Kitchen (mobile, often along Highland or by local schools)
This Dominican family-run truck rotates through Highland Avenue during lunch and late-night hours, serving rice bowls, empanadas, crispy fried plantains, and savory stews. Their pernil (slow-roasted pork) pairs perfectly with a sweet passionfruit juice. Follow their socials to stay updated on their exact locations — and don’t sleep on the tres leches cake!
International Cuisine: Big Flavors in a Small Neighborhood
Istanbul Express (730 Highland Ave)
The only Turkish spot in town, Istanbul Express captures the flavor of classic Middle Eastern cuisine at casual prices. The lamb gyro, chicken shawarma wrap, and homemade baklava come highly recommended. Vegan and vegetarian options abound — try the falafel platter or lentil soup. Lunch combos under $12 make this a great pick for a cozy dine-in meal or a filling takeout dinner.
House of India (corner of Highland Ave & Cottage St)
Relatively new to the area, House of India delivers bold curries, aromatic biryanis, and fresh-baked naan in a bright, welcoming space. Their buffet lunch (weekdays, $12) draws hungry crowds, while the butter chicken and samosas are the stars of the à la carte menu. Spice levels can be customized, and the mango lassi never disappoints.
Local Traditions and Classic Favorites
Highland Avenue is home to several family-run delis and diners that have become rituals for residents:
- Sammy’s Diner (501 Highland Ave): Classic American breakfast and comfort food, famous for generous portions and legendary pancakes.
- Highland Chinese Kitchen (624 Highland Ave): Neighborhood mainstay for take-out — loved for crispy egg rolls, savory fried rice, and quick service.
- Roma’s Italian Deli (528 Highland Ave): Hearty cold cuts, fresh mozzarella, and peppery arancini (rice balls) make this deli a cult favorite, especially for lunch.
Where to Eat Together: Community Hotspots
Several intersections along Highland Avenue blossom as social food hubs, especially near schools and places of worship:
- Wickham Ave & Highland Ave: Morning rush for bagels, coffee, and deli fare
- Highland Ave & North St: Best for grabbing lunch tacos, bakery treats, or a quick coffee
- Near Fancher-Davidge Park: Perfect for picnics or sampling street food from local trucks
Why Highland Avenue Is Worth the Trip
What sets this neighborhood apart is its balance of old-school charm and global variety. In just a few blocks, you can eat your way from New York’s Italian traditions to Mexican street food, Dominican classics, and Turkish delights. Each spot is run by passionate owners who greet regulars by name and newcomers with genuine hospitality — a true reflection of Middletown’s welcoming spirit.
So next time you’re searching for new flavor experiences, put Highland Avenue at the top of your must-visit list. Go with an appetite and an open mind — and you’ll discover your new favorite eats in this slice of Middletown.