The winning formula at Trina’s Starlite Lounge blends a retro dive bar with gonzo comfort food. This Inman Square neighborhood spot, just over the Somerville line, is worth seeking out any night of the week, but to truly experience Trina’s, take a Monday off for brunch. That’s when you’ll find the rowdiest crowd reveling in plucked-from-childhood comfort food like Pizza Bagels and House-made Pop Tarts, alongside a nationally renowned plate of Fried Chicken & Buttermilk Waffles. At all hours, the Trina’s bar is one of the best for craft cocktails like Fallen Angel, with tequila, jalapeño syrup, mango, lime, and a barbecue-dusted rim; and Matt’s Quickie, a Nesquik-inspired brunch drink.

Before Ana Sortun was a James Beard award-winner and co-founder of Sofra and Sarma, she debuted Oleana. The acclaimed chef’s original restaurant in Cambridge—which is technically situated off the edge of narrow Inman Square, but it’s so good we’ll include it in any relevant guide—feels as fresh as ever. Oleana keeps us coming back for its spice-packed takes on Middle Eastern meze, like the crispy, tender Spinach Falafel with beet tzatziki; and the sticky-sour-sweet-smoky Sultan’s Delight short ribs. Two other reasons we constantly want to return? One of the city’s best patios, and the surprising triumph that is the Baked Alaska dessert.

Christina’s Homemade Ice Cream may lack the sexy design and slick branding of the new-wave ice cream shops springing up across Camberville (it currently doesn’t even have a website), but this Inman Square institution has been experimenting with flavor since 1983. Around 50 ice creams are on the menu each day, with evergreen delights like Green Tea, Burnt Sugar, and an actually-tastes-like-the-real-thing Banana alongside frequently changing flavors. Christina’s also maintains a 33-flavor-strong list of seasonally rotating sorbets to satiate any dairy-free sweet tooth, too.

One of the first chef-driven restaurants to open in the neighborhood, Will Gilson‘s Puritan & Company finds inspiration in rustic New England traditions while borrowing liberally from world cuisine. That explains how Berkshire Pork Belly and harissa-honey Roasted Carrots share space on the menu with next-level Waygu Tri-Tip Carpaccio and Swordfish Pastrami Toast. This isn’t some precious, white tablecloth place, however. It’s casual and lively, with a great wine selection, whimsical desserts, and a street-side patio. Since making his name in Inman Square, Gilson has expanded with three place-making restaurants in a new development nearby called Cambridge Crossing.

Parlor Sports is “Not Your Average Sports Bar.” Sister restaurant to next-door Trina’s Starlite Lounge, it’s another home run for the ownership team including legendary local bartender Josh Childs and chef Suzi Maitland. The food menu at Parlor is filled with crowd favorites like Classic Parlor Nachos, piled high and perfectly layered with homemade tortilla chips, creamy cheese, and all the fixings; or a good ol’ Griddled Dog. Hunker down for the game with a pitcher of craft beer from the rotating selection, or slide in for a quick “Porch Beer,” which is Parlor parlance for crushable cans like Miller High Life. There are cocktails and shots, too. Besides the quality food and drink, what sets Parlor apart is that it’s truly for everyone, even non-sports fans (just see it on Bachelor night). Everyone here is on the team rooting for a good time.