Get the night going at Montana’s Trail House (445 Troutman St., at St. Nicholas Ave.; 917-966-1666); sip a craft cocktail like the Gin & Jam (seasonal jam, gin, and lemon juice) in the cozy private-library-esque bar and line your stomach with a relatively healthy meal (arctic-char tartare with popped sorghum; pea shoots with fennel).
Head to Left Hand Path (89 Wyckoff Ave., nr. Hart St.; no phone); stop by for a tap beer like Captain Lawrence’s Kolsch and Shiner’s Ruby Redbird (both $6), and admire the Solo-cup-like chandeliers and irreverent Justin Hager paintings of R. Kelly while juicing up your phone for the evening with the below-bar outlets.
Cocktail bar June (259 St. Nicholas Ave., at Menahan St.; 347-240-8118) is your last stop before full-fledged debauchery. If you’ve already overdone it at this point, soak up some of the booze at ’90s throwback Pizza Party (254 Irving Ave., nr. Bleecker St.; no phone). Snack on Hawaiian shirt pizza; Magic 8 Balls rest on tables.
The Pizza Party people also own Boobie Trap (308 Bleecker St., at Irving Ave.; 347-240-9105) across the street. A pink neon sign above the bar advises patrons to Fuck Off probably best to ignore it and take in all the breasts (there’s a mammary theme, including a topless mannequin spirit animal and a disembodied-boob ceiling fixture in the bathroom).
It’s time to take a little breather at Central Station (84 Central Ave., nr. Jefferson St.; 718-483-9884). The managing partner used to work at Fatty ’Cue, and there’s a similar laid-back feel; in the train-station-inspired room, drink a beer like Otter Creek’s Copper Ale or the cocktail of the day.
At Alphaville (140 Wilson Ave., nr. Suydam St.; 347-413-8801), you’ll find a brighter version of the hood’s divey institution Alaska (from its co-owner Skyler Insler). The vibe is as surreal and monochrome as its cinematic namesake; get a beer and a shot ($6) and vibe to live music and DJs (expect local and Euro-experimental-electro and retro-themed dance parties).
Once you’ve caught your breath, spend the rest of the night breaking a sweat with Brooklyn’s dance-ravers at Tropicalia-themed Bossa Nova Civic Club (1271 Myrtle Ave., at Hart St.; 718-443-1271), which just reopened after renovations. The party will probably still be going strong; look out for musicians and DJs like Alvin Aronson.
Post-dancing, head to Amancay’s Diner (2 Knickerbocker Ave., at Morgan Ave.; 718-628-8860), a 24-hour diner-slash-bar. In the Max Cellar downstairs, things get weird (recent event: sex-toy bingo). Upstairs, play a tabletop-affixed game of spin the bottle. Should things really get out of control, brunch starts at seven.