October 23, 2026

New Restaurants Join Downtown Middleton’s Dining Scene

2.4 min read| Published On: October 23rd, 2026|

By Gina Horan

New Restaurants Join Downtown Middleton’s Dining Scene

2.4 min read| Published On: October 23rd, 2026|

Downtown Middleton is filling in, and several of its newest arrivals involve food. Piesanos Stone Fired Pizza, Smalls Sliders and Jersey Mike’s Subs have joined the restaurant lineup, while Woodrow’s Duckpin has added bowling to the evening’s possibilities.

Piesanos opened earlier this month, becoming the company’s third restaurant in The Villages, alongside Southern Trace and Lake Deaton. Its menu centers on stone-fired pizzas, calzones and pasta dishes. The new location includes a separate takeout entrance, giving customers collecting orders their own route through the restaurant.

Smalls Sliders takes a narrower approach, building its menu around cheeseburger sliders, waffle fries and milkshakes. Its opening was announced earlier this month, following Jersey Mike’s arrival in August. Both add quick-service meals to a downtown district that has been steadily filling its dining rooms.

Woodrow’s Duckpin, open since September, adds a different kind of gathering place downtown, pairing bowling with a full bar serving cocktails, beer and wine. Guests can bring in outside food, making it possible to pick up a meal nearby and settle in for a game.

Duckpin uses shorter lanes, smaller pins and palm-sized balls without finger holes. Players get three rolls per frame instead of two, and there’s no need to rent bowling shoes. Lounge seating and televisions leave room for those who would rather watch the competition than join it.

The openings follow other additions this year, including Haru Japanese Restaurant, serving sushi, sashimi and hibachi, and Fiesta Grande Mexican Grill, which also has a location in Brownwood Paddock Square. Zunzibar opened in June and features fresh seafood, cocktails, outdoor seating and a late-night menu.

For anyone who hasn’t visited recently, those businesses now share downtown with 4 Rivers Smokehouse, Portillo’s and Victory Sports Grill. Abbott’s Frozen Custard is also open for anyone whose plans start or end with dessert.

Among the earlier arrivals this year was 24 Middleton, the neighborhood bistro from Jordan McDonough and Jonathan “JT” Tubby, who also own Edna’s on the Green. Its open kitchen and chef’s counter put the cooking in view, with a menu shaped by the owners’ hospitality experience and travels.

More restaurant spaces remain in progress. China Taste, Coffee for the Soul and The Great Greek are listed as coming soon in Middleton’s current downtown directory, with opening dates still to be confirmed.

Photos by Gina Horan

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About the Author: Gina Horan

Gina moved to Central Florida from the San Francisco Bay Area in 2021. She holds a degree in linguistics and has worked as a fashion editor, photo stylist, lifestyle columnist and food writer since 1995. She later covered travel, events, restaurants, music festivals and sports throughout Northern California, including work as a morning show host with KSAN radio and food critic for KRON Bay TV. A veteran bartender, she has worked in hospitality on and off since high school. Gina joined Akers Media in 2022 and is currently the Food and Lifestyle Editor. Her passions include travel, road trips, history books and podcasts, tasting menus and arriving in a new city without a map.

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