Best Group Dining Gatherings Italian Restaurants in Old Town
3 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
Topo Gigio Ristorante
High-energy Old Town classic with a deep pasta menu and busy patio.
Notable Picks
8.2
Topo Gigio is an Old Town standby where a sprawling menu of classic pastas and red-sauce plates is backed by a busy dining room and brick-walled patio. It’s the move for group dinners and lively dates that prioritize big portions and familiar flavors over hushed conversation.
Must-Try Dishes:
Fusilli alla Topo Gigio, Conchiglie alla Sarda, Tortellini alla Panna
What makes it special: High-energy Old Town classic with a deep pasta menu and busy patio.
Gussie's Handmade Italian focuses on fresh pastas, seasonal sauces, and cocktails in a modern Old Town space just off North and Wells. It fills a niche between neighborhood trattoria and special-occasion spot, with enough polish for dates but a menu flexible enough for casual plates at the bar.
Must-Try Dishes:
Rigatoni Pomodoro, Brown Butter Honey Ravioli, Linguine al Limone with Shrimp
What makes it special: Handmade pasta and seasonal seafood plates served with a cocktail-focused bar program.
Worthy Picks
#3
Orso's
7.9
Orso's Italian Restaurant has served Old Town for decades with a long menu of pastas, chicken dishes, and pizzas in a classic dining room and grapevine-covered patio. Regulars lean on familiar standards and relaxed, slightly nostalgic energy more than chef-driven reinvention.
Must-Try Dishes:
Lasagna Bolognese, Chicken Parmesan, Salmon Vesuvio
What makes it special: Long-running Old Town stalwart with a leafy patio and crowd-pleasing classics.