Bars in Chestnut Hill

Select Local Merchants

The Urban Grape pushes the fermented philosophy that wine and beer drinkers should explore its vast variety of flavors without intimidation. The shop’s extensive lineup of red wines ranges from the dark-chocolate aromas of Charles Krug’s cabernet sauvignon from Napa Valley ($24) to the full-bodied O.Fournier tempranillo from Spain ($16). Have the ideal white wine for a gorgeous afternoon firing nukes at incoming asteroids with the Ken Forrester chenin blanc from Stellenbosch ($10), boasting subtle grapefruit and green-apple notes. Beer buffs may blissfully quiver while looking at The Urban Grape’s selection of brews, including a 22 oz. Brew Dog Punk IPA from San Diego ($7). The store offers a number of other libations as well, from organic and biodynamic wines to a stellar array of sake. Drop by for The Urban Grape’s scheduled complimentary wine tastings every Thursday and Friday from 5 p.m.–7 p.m. and every Saturday from 1 p.m.–3 p.m. to introduce taste buds to up to 16 different types of wine.

7 Boylston St
Chestnut Hill,
MA
US

Though Yelpers have mixed feelings about the sometimes-noisy atmosphere, they praise The Playwright’s food and give it a three-star average. Nine Citysearchers give it an average of four stars.

1960 Beacon St
Brighton,
MA
US

Charley's invites diners to taste a sprawling menu that features American classics such as steaks, seafood, and salads. Hand-cut french fries are served alongside burgers piled with bacon, crisp fried onions, and enormous pickle slices. As forks and knives dig into steaks forged from USDA choice beef, aged a minimum of four weeks, a wine list details more than 60 different wines available in bottles and glasses, instead of a server’s boots. During weekend mornings, brunch details specialties such as thick-cut french toast, filet-mignon benedict, and corned-beef hash, served with spicy bloody marys, mimosas, or champagne.

199 Boylston St
Chestnut Hill,
MA
US

Devlin’s dishes out upscale cuisine in a friendly and casual atmosphere, pampering patrons with a menu stocked with innovative twists on traditional fare. Philly cheesesteak spring rolls come partnered with smoky chipotle sauce ($10), and lobster penne marries fresh seafood and pasta using a flavorful marsala cream sauce as both ring bearer and maid of honor ($23 for large, $14 for small). For a sharable snack that doubles as a flightless Frisbee, try a crispy pizza topped with prosciutto, fig jam, and blue cheese, with caramelized onions and arugula officiating the taste-bud tug-of-war between savory and sweet ($14). Though Devlin’s has convenient night-owl hours, the weekly Sunday jazz brunch lets early birds practice their sophisticated snaps whilst pecking at sleep-betraying orders of eggs benedict served with canadian bacon ($10) or soul-satisfying portions of challah french toast drizzled with Vermont maple syrup, served with bacon, sausage, or ham ($10).

332 Washington St
Brighton,
MA
US

The menu at Porter Belly's Pub is packed with savory, soul-satisfying eats. Dig into a plate of homemade pork sausages, grilled to deliciousness with dried cranberries, garlic, and herbs ($8). Each of the nine signature burgers—such as the Alamo with roasted red pepper and monterey jack cheese—comes with your choice of a beef, chicken, turkey, or veggie patty ($9). Entrees include a hearty portion of shepherd's pie made with fresh ground beef and select vegetables in home-style gravy. This particular pie also is accompanied by a heaping helping of mashed potatoes layered with melty cheese ($9.95). Saturday night's ailments can be cured with a time machine or a hearty Sunday brunch, served from noon to 3 p.m. This Groupon is also valid toward Porter Belly's Pub's prix fixe neighborhood menu.

338 Washington St
Brighton,
MA
US

The chefs at Bamboo Thai Restaurant developed a menu that gives diners complete control over their gustatory experience, from the level of spiciness to the type of noodles accompanying their dish. Five distinct curries—red, green, yellow, panang, and massaman—pair with the guest's selection of one of nine proteins and one of 10 rice or noodle options, including udon, buckwheat, and vermicelli, resulting in more dinner options than a socialite's rolodex. The noodle selection process crops up again when ordering one of the six meal-in-a-bowl soups, and five pad thai options dare taste buds to pick from vegetables, chicken, shrimp, or a combination of all three, with rice or crispy egg noodles. To complement spicy bites, a lengthy list of Thai, Japanese, and American beers stands next to warm and draft sakes.

1616 Commonwealth Ave
Brighton,
MA
US