Friday, May 1 — Taste of the North End. The restaurant-lined, Italian-heavy North End may teem with tourists, but born-and-bred Bostonians find great meals there too — if they know where to look. (If not, check out our neighborhood guide.) For a taste — or rather, tasting — of what the 'hood has to offer, graze among the 35+ participants in tomorrow's Taste of the North End, held at DCR Steriti Memorial Ice Rink (561 Commercial Street). Some of the top spots doling out bites are Bricco, Mamma Maria, Neptune Oyster, Taranta, Tresca and Ward 8. Plus: beer and wine, a silent auction, and emcee Jenny Johnson, host of NESN's "Dining Playbook." Tickets are $99 here and benefit multiple North End non-profits. It kicks off at 7 PM.
Friday, May 1 through Sunday, May 10 — Acoustic on Main at Boston Chops. Restaurateur Brian Piccini (he's also behind dbar and Deuxave) happens to be a classically trained pianist. So perhaps it's no surprise that his South End steakhouse (pictured at top) will take part in "Acoustic on Main," a campaign to bring live music from local artists to area businesses. If you want your a la carte chops served with a side of soothing tunes, Boston Chops will feature a different performer every night during the series, from jazz to show tunes, Celtic tunes to electronic pop-dance. Piccini himself will tickle the ivories on select nights. Performances will be staged from 6-9 PM nightly.
Saturday, May 2 — Kentucky Derby Party at Drink. Something something horses, something something hats. Let's be honest: For most northerners, the Kentucky Derby is just about day-drinking. And though many bars and restaurants are throwing special events, we'd place our bets on this Barbara Lynch-owned cocktail joint, which will host a party from 3-7 PM that feature stationary and passed bites, commemorative glassware for guests, contests for "best hat" and "best limerick", and three drinks included in the $80 ticket fee. ($10 per drink beyond that.) Reserve your spot by calling 617-695-1806.
Monday, May 4 — Revenge of The Zombie at EMPIRE Restaurant and Lounge. Jeff "Beachbum" Berry is regarded as a legend in the rum and tiki cocktail circuit. One of his finest feats: cracking the code of tiki pioneer Donn Beach's original, closely-guarded recipe for the now-iconic Zombie. In a special class at this Seaport pan-Asian and nightspot (pictured), Berry will share his discovered secret with a private class — over complimentary drink samples and food pairings, of course. For an audience with the master (two sessions: 6:30 PM and 8:30 PM), get $55 tickets here.
Monday, May 4 through Sunday, May 10 — Boston Bakes for Breast Cancer. Until there's a cure, there'll be this annual event that brings together restaurants around the city — and beyond — to support vital research and treatment programs at Dana-Farber Cancer Institute. How it works: Over 300 statewide restaurants and bakeries designate a specific dessert that will cut a portion of the proceeds to the campaign with each purchase. But some eateries go the extra mile, joining the "50% Club" and donating a full half of the monies from each purchase of any dessert item. Among those "Club" members: ArtBar, Bokx109, Centre Street Cafe, Todd English's Figs and Zebra's Bistro and Wine Bar.
Thursday, May 7 — The Maine Course at Artists for Humanity EpiCenter. Because every kid deserves a chance to develop self-esteem, leadership skills and a commitment to service, this foodie-focused fundraiser will support Agassiz Village, a Maine summer camp that helps children from underserved communities experience an enriching opportunity away from city life. (90% of campers live at low-income or poverty levels.) The South Boston events venue at 100 West 2nd Street will host bites from local chefs, spirits from Bully Boy Distillers and brews from Sam Adams from 6-9 PM. Participating restaurants include Bastille Kitchen, Commonwealth, Loco Taqueria & Oyster Bar, Menton, Townsman and West Bridge, to name a few. Tickets are $150 here.
Monday, May 11 through Sunday, May 17 — Cape Cod Restaurant Week. We're always happy to share reasons to drive to Cape Cod. Here's another one (which mercifully precedes the post-Memorial Day traffic uptick): Cape Cod Restaurant Week, uniting a record 42 restaurants throughout the region. They'll offer 3- or 4-course prix fixe meals for just $25, $30 or $35. Even accounting for gas, you'll come out ahead. You can find the full list of participants at the website, but a few standouts include Falmouth gastropub Bear in Boots, Provincetown eatery Fanizzi's, and the classic Old Yarmouth Inn.
Wednesday, May 13 — Seaport Sangria Smackdown at the Seaport World Trade Center. Because Spring is time to break out the patio furniture and pitchers of sangria, more than half a dozen restaurants will send bartenders to compete for bragging rights of the best sangria: Legal Test Kitchen, M.C. Spiedo, Sam’s and The Barking Crab are among the participants. Head over from 6-8 PM for noshes and sample-sized sips, then vote for your favorite. Tickets are $20 here.
Wednesday, May 13 through Sunday, May 17 — Nantucket Wine Festival. Need an excuse to make an early trip to ACK? This multi-day extravaganza of sipping (there are tastings and session covering everything from Bordeaux to bubbles), slurping (oyster flights!) and supping at in the "culinary tent" and at special food events — like a barbecue with Tremont 647 toque Andy Husbands. For the full lineup and ticket options, head here.
Friday, May 29 & Saturday, May 30 — American Craft Beer Fest at the Seaport World Trade Center. Over 640 craft beers, reflecting 140 national brewers. You don't have to work tomorrow. The end. (For tickets to three different weekend sessions, $50 each, head here.)