Before Sofra and Sarma, there was Oleana. Now in its 18th year, Ana Sortun’s original restaurant feels as fresh as ever and keeps us coming back for its spice-packed takes on Middle Eastern mezze. The perfectly cooked Spinach Falafel with beet yogurt is reason to visit in itself, but we’ll throw in two more: one of the city’s best dining patios and a surprising but oh-so-worth-it take on a Baked Alaska.
If you only think of Inman Square as a middle ground between Central and Union, you’re doing it wrong. This neighborhood straddling the Cambridge-Somerville border is a microcosm of what makes each city great, from chef-focused independents to funky local favorites.
The formula that blends a dive bar with gonzo comfort food at Trina’s Starlite Lounge is worth seeking out any night of the week, but it truly shines during Sunday and Monday brunch. That’s when you’ll find plucked-from-childhood fare like Pizza Bagels and House-made Pop Tarts alongside a nationally renowned plate of Fried Chicken & Buttermilk Waffles. Wash it all down with the Matt’s Quickie, a Nesquik-inspired concoction made with vodka, coffee liqueur, instant chocolate milk, and an optional float of Green Chartreuse.
Christina’s Homemade Ice Cream may lack the sexy design and slick branding of the new-wave ice cream shops springing up across town, but this Inman Square institution has been experimenting with flavor since 1983. Around 50 ice creams are on the menu each day, and while flavors frequently change, triumphs like Green Tea, Burnt Sugar, and an actually-tastes-like-the-real-thing Banana, are evergreens. 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 but borrows liberally from world cuisine. That explains how Wild Mushroom Toast shares space on the menu with next-level Prime Beef Tartare and Swordfish Pastrami topped with mustard ice cream. Lest you might accuse the spot of being precious, head here on a Sunday to snag the 10-ounce Prime Rib complete with salad, hearty sides, and even an ice cream sundae for dessert.
Most wine bars aren’t known for their fried chicken, but BISq (a.k.a. “Bergamot in Inman Square”) isn’t most wine bars. Here you can select something by the glass from a substantial French- and German-centric wine list before pairing it with a small plate like the Maitake Mushrooms with cured egg yolks, or tuck into substantial fare like the Double Cheeseburger with fried shallots and special sauce. Our favorite combination draws from both sides of the menu: The House-made Ricotta and the crispy Fried Chicken are two different dishes that work best as one.