01
Best overall pick
Corbo's Pasta & Pizza House
Near Richmond Road Corridor • Classic Italian-American Pizza Joint • Go-To For Highland Hills Locals
A reliable, no-nonsense spot for hearty pies and pasta just minutes from the center of Highland Hills.
Corbo’s is the kind of place people around Highland Hills call first when they need pizza for family, coworkers, or a game night. The crust is sturdy enough for generous toppings, the sauce leans savory and comforting, and the menu is big enough to keep non-pizza eaters happy with pasta and subs. It’s unfussy, consistent, and close enough that delivery or carryout is almost always the easiest option.
02
Best for big orders and game days
Romeo's Pizza Highland Heights
Highland Heights • Neighborhood Chain Pizzeria • Top Choice For Crowd-Pleasing Delivery
Thick, cheesy pies and specialty combinations make Romeo’s a staple when you’re feeding a crowd.
A quick drive up the hill to Highland Heights gets you to Romeo’s, a regional chain that East Siders trust for dependable, shareable pizza. The dough has a soft, bready chew, the toppings run generous, and the specialty pies—like loaded meat options or veggie-heavy combinations—take the guesswork out of ordering. Late hours and efficient delivery make it especially handy for game nights, study sessions, or last-minute office orders.
03
Best sit-down night out
Crostatas Pizzeria
Highland Heights • Neapolitan-Style Italian Restaurant • Best For A Relaxed Dine-In Experience
A cozy Italian spot known for its thin, wood-fired pies and small plates that feel a step above typical takeout.
Crostatas is where you head when you want pizza to feel like a proper night out rather than just a quick box on the counter. The menu leans Italian, with crisp, thin-crust pies that show off charred edges, balanced toppings, and good olive oil. Pair a pizza with a small plate or salad, stretch out over a carafe of wine, and you’ve got a date-night-level experience still close to Highland Hills.
04
Best for creative toppings
Totally Baked Pizza
East Side Suburbs • Casual, Build-Your-Own Pizzeria • Best For Adventurous Eaters
A playful shop that leans into bold toppings and hearty crusts for pizzas that feel a little over-the-top in the best way.
Totally Baked caters to people who like to push beyond standard pepperoni and cheese, with a menu full of loaded specialty pies and plenty of options for custom builds. Expect thick, satisfying crust, generous cheese, and combinations that range from barbecue-inspired to veggie-packed. It’s a fun choice when you’ve got a mixed group and want everyone to walk away with something tailored to their tastes.
05
Best East Side destination pie
Dewey's Pizza Shaker Heights
Shaker Heights • Contemporary Craft Pizzeria • Worth-The-Drive Specialty Pizza Spot
A polished, family-friendly restaurant with inventive specialty pies and a well-run dining room in the Van Aken area.
If you’re up for a short drive from Highland Hills, Dewey’s in Shaker Heights delivers some of the most consistent, creative pizza on the East Side. The crust sits in that sweet spot between chewy and crisp, and the menu leans into clever topping combinations without feeling fussy. With friendly service, a good beer list, and a lively but organized dining room, it’s a smart pick when you want pizza to anchor a night out rather than just fill a box.