Time Out Love New York Awards 2014: Upper West Side

The two sides of upper Manhattan have a rich history of one-upmanship, competing over high-society concerns like private-school acceptance rates and whose money is the oldest. Nightlife has never played much of a role in this posturing, until a recent spate of offbeat bar openings (Jones Wood Foundry, City Swiggers, Earl's Beer and Cheese) suddenly brought legitimate buzz to the Upper East Side. Consider Jacob's Pickles a retort from across the park. With a lot of ground to make up, it's not surprising the craft-beer-and-biscuit--slinging gastropub is trying a little too hard, shoehorning a grab bag of tippling memes—Dixieland grub, house-made bitters, wines on tap—into one rustic barroom. But while the results are hit-and-miss, the spot's instant crowds speak for themselves: The 'hood's drinkers need a pick-me-up, and for fans of pickles and beer, Jacob's is doing its part to raise the bar. DRINK THIS: Once you get over the inflated prices ($7--$9 for a 15-ounce pour), you'll find that the bar's 25 taps offer uptown brew geeks plenty to get excited about. The all-domestic lineup is broken down by state, with a stable of Northeast breweries (Pretty Things, Allagash) complemented by cross-country favorites: the silky Maduro Oatmeal Brown Ale ($7) from Cigar City in Tampa, plus Stone's Cali-Belgique ($8)—a hoppy Californian IPA brewed with Belgian yeast. The cocktail program, heavy on infused spirits and pickle juice, is too spasmodic, meddling with the Manhattan (made here wit

Upper West Side caffeine fiends can sip single-origin espresso at this 74-seat brownstone café, the third location from the Hudson Valley coffee roaster. The shop also brews pour-overs through Japanese Kalita drippers, and offers light fare, including bagels, salads and sandwiches. Nighttime drinkers looking for a boozier buzz can choose from wines and local craft beers.

This community bookstore goes above and beyond to make itself a destination for reading and playing alike. In addition to its inviting children's room, packed with puzzles, art supplies and toys, the UWS store attracts mini literati in droves with its weekend storytelling sessions, often featuring guest appearances by kid-lit authors. Its other branch, on 112th Street, carries a small selection of children's books too, but isn't a kid mecca like this one is.

There is no mistaking the theme at this Upper West Side bar: Framed literary verses and portraits of writing greats hang from exposed-brick walls. Specialty cocktails bear names like the Edgar Allan Poe (vodka, triple sec and lemon) and the Jack Kerouac (tequila, blue curaçao, fresh lemon and lime), while Guinness—poured with a shamrock carefully drawn into its foam—anchors the 13 taps and an extensive Irish whiskey selection that would make any heavy-drinking writer proud. Grab a classic from the small in-house library to skim before the rowdier night crowd arrives.

Resplendently restored, this spacious former vaudeville theater hosts a variety of popular acts, from Emmylou Harris to ZZ Top; once a year, the Allman Brothers take over for a lengthy residency. While the vastness can be daunting to performers and audience alike, the baroque, gilded interior and uptown location make you feel as though you’re having a real night out on the town.