Holiday season is upon us once again, and for many, that means braving the soul-deadening suburban shopping malls while grabbing quick bites at their food courts, chain restaurants, or, preferably, indie spots in or near the malls. For others, it may mean hitting some of the newer mixed-use developments in and around Boston, which, while generally more pleasant and often with good dining and drinking options, can also be stressful due to traffic, parking lots that are full, and hordes of people, with no real escape. 

Unlike so many other cities, however, Boston (as well as the surrounding communities) has some vibrant, interesting, and charming neighborhoods where people can do their holiday shopping in a much more enjoyable manner, and because they are actual neighborhoods, there are typically plenty of cozy little local spots to duck in out of the cold to grab a bite to eat or drink. Several such areas are mentioned below, with a couple of options for each neighborhood.

South End

Few neighborhoods in Boston are more attractive than this one, and tourists, college students, and others who may be new to the area tend not to know about the South End because it’s just a bit off the beaten path compared to, say, the North End or the Back Bay. Shopping options abound here, including specialty food shops, antique stores, and art galleries. A can’t-miss event for shoppers and strollers alike is the SoWa Winter Festival, which takes place in early December and where you could conceivably take care of all your shopping in one afternoon. Dining and drinking options are everywhere in the South End, with a local fave being Metropolis (584 Tremont St), a downright romantic eatery that features some outstanding Mediterranean and New American fare, including butternut squash and apple risotto, seared duck breast, and rigatoni with sausage along with an impressive list of wines. If you’re looking for something a bit more down and dirty but still with a local bent, Anchovies (433 Columbus Ave) is an absolute treasure with its old wooden booths, huge plates of Italian food, and rather interesting people-watching at the bar. 

North End

The North End gets a bad rap, perhaps because it’s such a popular spot for tourists, business travelers, and others who don’t live in the region, but it remains one of Boston’s great neighborhoods for walking, dining out, and shopping. And if you need to do holiday shopping, Hanover Street and the lesser-traveled Salem Street a block north are ideal spots for finding gifts of all kinds, including baked goods and pastries. If you get a bit tired of shopping or walking and want to hit more of a local hangout for a meal, Al Dente (109 Salem St) is a marvelous option, especially if you love good old-fashioned Italian-American cuisine. This narrow little eatery has all the classics, from pasta dishes to chicken, veal, and seafood, and if you want to really feel like a regular, order a glass of Campari or another Italian liqueur to go with your meal. For those looking for more of a dessert/coffee place, Caffe Vittoria (290-296 Hanover St) is almost like a living museum with its tin ceiling, old photos and posters, liqueur and cigar bars, and some of the best cappuccino and espresso in the region along with biscotti, which is a must if you order a coffee drink or perhaps a hot chocolate. 

Beacon Hill

As you approach the holidays, this wealthy pocket of the city looks like something out of a calendar, with its gas lamps, light displays, and decorations combining with the historic architecture to make for the type of atmosphere you rarely see in American cities. Charles Street is the main commercial strip and is lined with great little independent shops if you don’t mind paying a bit extra for gifts, but interestingly enough, when it comes to dining out or drinking, some relatively reasonable options exist here. Beer lovers should check out The Sevens (77 Charles St), a former dive bar that still has the feel of an unpretentious neighborhood joint. Along with its mix of top craft beers and mass-market brews you’ll find some really good pub grub, including wings, nachos, chili, toasted sandwiches, and a knockwurst plate that goes perfectly with a beer or two. A slightly higher-end spot—but still casual—is a hidden local fave called 75 Chestnut (75 Chestnut St), which years ago had been a special occasion spot but is now a slightly upscale restaurant featuring American classics. Whether you sit at the homey little bar area or in the quiet dining room, you can choose from such options as steak tips, burgers, pork chops, a steak sandwich, and seafood stew, while the bar side has a good selection of beer and wine along with all kinds of lower- and higher-end spirits.

Coolidge Corner, Brookline

Brookline has some great neighborhoods for wandering, and Coolidge Corner may be the best if you’re looking to do some gift-buying. Both Harvard Street and Beacon Street have ma-and-pa stores as far as the eye can see, and you may notice that all kinds of restaurants and bars are mixed in among the shops as well. One of the best choices in Brookline—if not all of the Boston area—is Ganko Ittetsu Ramen (318 Harvard St), an extraordinary ramen shop hidden away in the historic Arcade Building that will make you forget about all the drunken nights eating 99-cent ramen after the bars closed back in college. The menu is a small one, as is the space, but it is tough to think of anything better than a piping-hot bowl of tan tan ramen with ground pork on a chilly late fall day. Another hidden gem of sorts is an overlooked spot a few blocks north of Coolidge Corner called Brothers Restaurant (404 Harvard St), an oddly set up two-room place where the right storefront is a bar area and the left storefront is a dining area, with the two being nearly completely separated from each other. Brothers is a calm and serene place that is perfect for quiet conversation, and such New American dishes as short rib tacos, braised lamb shank, pan-seared rare rare Ahi tuna, and brick chicken are top quality and very reasonably priced.

Harvard Square, Cambridge

Cambridge’s best-known square has been in the news of late for all the wrong reasons, as much of the square seems to be in the process of being gutted and turned into a place filled with chains and high-end shops. But Harvard is still a special spot with lots of great places for shopping if you look hard enough, and this also goes for dining and drinking options. A popular local spot that is just far enough away to keep it a secret from tourists and other travelers is Cambridge Common (1667 Mass Ave), a warm and inviting beer bar with a huge wraparound bar dominating the space. The food here is quite impressive, including some of the best boneless buffalo wings in town and equally good wings, and for those who lover tater tots, the tots here go really well with beer. Speaking of which, this is perhaps one of the oldest gastropubs in the Boston area, and the ever-changing beer list is something to behold, including some rare ones from local and regional breweries. If you’d rather be a bit closer to the heart of the square, The Boathouse (49 Mt Auburn St) is an under-the-radar spot that is nothing like the meat market by the same name on JFK Street from years ago, instead being a mellow restaurant and bar with a nautical theme and some Irish leanings. This version of the Boathouse (which indeed has no connection to the “other” Boathouse) features all kinds of comfort food, including great takes on macaroni and cheese, fish and chips, shepherd’s pie, and bangers and mash.