01
Best overall pick
Dewey's Pizza – Kenwood
Kenwood Towne Centre Area • Creative Artisan Pizzeria • Best For Families
Creative specialty pies, an open kitchen, and friendly service make Dewey's in Kenwood the easiest crowd-pleaser near Highpoint.
This is the spot you pick when everyone in the group wants something a little different but no one wants to gamble. Dewey's is known for its well-balanced toppings, chewy-crisp crust, and build-your-own flexibility, plus half-and-half pies that keep the table happy. It’s close enough to swing by after a Kenwood Towne Centre run, and the upbeat, family-friendly room handles kids and larger groups without feeling chaotic.
02
Best for bold flavors
Taglio Bar + Pizzeria – Montgomery
Montgomery • Detroit-Style Bar Pizzeria • Best For A Night Out
Taglio serves thick, caramelized-edge Detroit-style squares with big toppings and a lively bar vibe.
If you like your pizza rich, crispy, and a little over-the-top, Taglio is worth the short hop from Highpoint into Montgomery. The signature Detroit-style pies come in airy, focaccia-like slabs with lacy cheese around the edges and toppings that lean indulgent, from pepperoni cups to loaded veggie combos. With a full bar, TVs, and a buzzy dining room, it doubles nicely as a low-key date spot or game-day hangout.
03
Classic East Coast feel
Brooklyn Pizza & Pasta
Montgomery Corridor • Classic New York–Style Slice Shop • Local Weeknight Favorite
Foldable New York–style slices and generous pasta plates give this Montgomery mainstay a no-nonsense, neighborhood feel.
Brooklyn Pizza & Pasta is the kind of place where you walk in, point at the pies in the case, and know exactly what you’re getting. The crust stays thin and sturdy enough to fold, the sauce leans classic and garlicky, and the toppings skew familiar rather than flashy. Locals use it as a dependable weeknight option for takeout slices, stromboli, or a big baked pasta that feeds a small crowd from Highpoint with minimal effort.
04
Best value for big appetites
Fratelli's Pizzeria – West Chester
West Chester And Tylersville Road • Casual Neighborhood Family Pizzeria • Worth-The-Drive Classic
A relaxed strip-center shop turning out saucy, topping-heavy pies that are built to share and travel well.
Head a bit north from Highpoint and you hit Fratelli's, a low-key pizzeria where portions are generous and the menu leans comforting. The pizzas come with a slightly thicker, bready crust that stands up to extra cheese and toppings, and the wings and garlic bread knots make easy add-ons. It’s especially handy when you’re feeding a team, a birthday party, or any group that just wants plenty of classic pizza without overthinking it.
05
Destination pizza night
Two Cities Pizza Co.
Historic Mason • Dual New York And Chicago-Style Spot • Best Special-Occasion Pick
Two Cities turns the New York vs. Chicago debate into a fun theme, with standout versions of both deep-dish and thin-crust pies.
It’s a bit more of a drive from Highpoint, but many locals consider Two Cities a true destination for pizza. The menu is split between buttery, slow-baked Chicago-style deep dish and classic New York–style rounds, so you can settle the table’s crust preferences in one place. The playful, city-themed interior and polished service make it feel a notch more special than a typical strip-mall pizzeria, ideal for a Friday night out or showing off the local pizza scene to visitors.