Five things to eat, drink, see, hear, and do with your Charm City weekend.

 EAT

June 16: National Cannoli Day

Vaccaro’s Italian Pastry Shop, 222 Albemarle St. 9 a.m.-12 p.m. Free.

It seems like every day is some sort of obscure food holiday—National Rotisserie Chicken at the beginning of the month, National Jelly-Filled Doughnut Day just last week—and this weekend is no different. June 16 is National Cannoli Day, and fittingly enough, Little Italy is ready to celebrate with a smattering of the sweet stuff. All day Friday, head to the O.G. pastry shop, Vaccaro’s, for discounted deals on the authentic Italian favorite. Grab an espresso and indulge in a sugary shell (or two) of sweet ricotta cream—a great start to any hot summer night. 

 DRINK

June 17: Baltimore Wine Festival

Canton Waterfront Park, 3001 Boston St. 12-7 p.m. $10-95. 

Calling all vino lovers. The third annual Baltimore Wine Festival is back with more than 160 vintages from around the world. Seasoned sommeliers and Franzia fanatics alike can stroll through Canton Waterfront Park and enjoy everything from rieslings to rosés, with live music, cooking demos, and gourmet food from more than 30 area eateries, including crab cake sliders from Jimmy’s Famous Seafood, grilled sausages from Snake Hill, ice-cream sandwiches from Cream Cruiser, and ice-cold shucks from The Local Oyster.

 SEE

June 18-20: Clueless

The Senator Theatre, 5904 York Road. Sun. 10 a.m., Mon. 1 p.m., Tue. 9:30 p.m. $7-10.

You have something better to do on Sunday than go see this 1995 classic at our city’s beautiful retro cinema? As if! Roll with your homies to Belvedere Square, where The Senator will be playing a special screening of Clueless for three nights. This cult comedy follows the teenage trials and tribulations of Beverly Hills, as one of the most popular girls in school, Cher (Alicia Silverstone), has tasked herself with a multitude of adolescent challenges: fixing up her teachers, making over a new transfer-student friend, and passing a driving test among them. Relish in pre-Apatow Paul Rudd and get ready to mouth your favorite lines, like “And may I please remind you that it does not say ‘RSVP’ on the Statue of Liberty!”

 HEAR

June 17: Saturday Morning Tunes Family Festival

WTMD Studios, 1 Olympic Pl., Towson. 9-11:30 a.m. Free-$15.

Music festivals aren’t just for grown-ups. Now, thanks to the radio wizards at WTMD, kids in Baltimore have their very own concert, tailored just for them. On Saturday morning, head to Towson to join the station’s latest show, “Saturday Morning Tunes,” for a few hours of live music. Hear children’s musician and storyteller Barry Louis Polisar (of Juno fame), as well as SMT’s house band, The Cartunes, performing beloved cartoon theme songs from the likes of “Duck Tales,” “Bob the Builder,” and “Inspector Gadget.” Let the kids enjoy snacks, partake in arts and crafts with The Walters Art Museum, and take a spin around the plaza with the help of Race Pace Bicycles. School’s out for summer, indeed.

 DO

June 17-18: Baltimore Pride

Charles North & Station North. Locations & times vary. Free. 

This weekend, the heart of Baltimore will turn ROYGBIV. Follow the rainbow to Station North, as the 42nd annual Baltimore Pride relocates after more than 40 years in Mt. Vernon. In a brand-new neighborhood, celebrate the city’s LGBTQ community with a giant block party, the iconic high heel race, and a festive, float-filled parade. While you’re at it, kick it all off on Friday with the annual Twilight on the Terrace cocktail party at Gertrude’s, as well as a Pride-themed poetry slam at the Impact Hub. On Saturday, swing into one of many dance parties, with multiple DJs at Grand Central and the Queerology dance and film series at The Crown. And, of course, on Sunday, don’t miss the full-day festival and pool party at Druid Hill Park. 

As temperatures rise, there seem to be plenty of outdoor sipping celebrations planned across the region. But the annual Baltimore Wine Festival at Canton Waterfront Park, returning June 17, continues to stand out among the pack. “It’s such a picturesque venue,” says organizer Beth Laverick, who owns B. Scene Events and Promotions. “The waterfront is Baltimore’s trademark.”

Aside from the beautiful backdrop, Laverick mentions that the soiree’s family-friendly atmosphere, tiered ticket options, handmade goods for sale by area artisans, wine seminars, chef demonstrations, live music lineup, and array of local food vendors make it one of a kind. “I never want it to be focused solely on drinking wine,” she says. “There are a lot of other elements that make it really exceptional.”

The inaugural festival in 2015 drew a crowd of 4,000, and Laverick is expecting to accommodate more than 8,300 this year. She says that, as the festival evolves, she is most proud that it has become a summer tradition for locals and visitors alike. “It’s really a reflection of Baltimore’s local vibe and what we have access to,” says Laverick, who also organizes the annual end-of-summer Baltimore Seafood Festival, scheduled for September 16 this year. “You don’t find special events like this in every city.”

Here are a few new things to look for while strolling around this year’s wine wonderland:

A boost in featured wineries
Oenophiles will be happy to hear that the wine lineup has jumped from 140 to 160 this year, with samples ranging from worldly whites and reds to sangria and rosé. “The first year we didn’t order a lot of Moscato or sweeter whites because you don’t see them very often on menus around here,” Laverick says. “But we ran out immediately. So we’ve added a lot more of the refreshing, lighter, sweeter wines.” Meander around the grounds to mingle with local purveyors, as well as visiting vintners including California’s Delicato Family Vineyards.

An expanded music lineup
Nothing says summer like dancing in the grass with a glass of wine in hand, and this year the event has doubled the number of bands performing throughout the day. The diverse roster of local acts includes Americana and roots group The Crawdaddies, reggae rockers The Scotch Bonnets, and funk-fueled 8 Ohms Band. Laverick chose horn-heavy blues cover band Tumblehome to kick off the festival with the opening set: “They’re a bunch of local guys, who practice out of Living Classrooms and really love what they do. I love their local flavor.”

Additional eats from area restaurants
For Laverick, yet another way of stressing the local feel is through the festival’s food offerings. “I turn away the fried Oreo vendors because we’re not a fair,” she says. “We want to highlight the area’s best restaurants and food trucks.”

Vendors from the city and beyond will gather at the park to offer everything from steamed buns and barbecue to oysters and ice cream sandwiches. This time around, look out for new offerings including chicken salad sandwiches from Wicked Sisters, cheese plates and crab cakes from Firehouse Canton, colorful salads from Pasta La Vista, and shrimp salad sliders from The Local Oyster. Adds Laverick: “There are a lot of grab-and-go options for people who like to bring their blankets, find shade near the water, and camp out for the day.”

Early entry and mimosas for VIP ticketholders
Laverick says that the VIP ticket option—15 wine tastings and all-inclusive access to a private bar—has been a draw for many attendees since the inaugural festival. “The VIP is probably my favorite area of the event,” she adds. “You would think it would be so chaotic, but it’s actual really peaceful.” This year, VIP ticketholders will be admitted one hour early in order to avoid long lines at the entrance when the gates open at noon. Aside from early access to food vendors, top-tier ticketholders will also be able to enjoy complimentary mimosas, bagels, and pastries before the festival officially kicks off. Enter to win four VIP tickets to the festival here. 

Three new local breweries
We know, we know. A wine festival is all about the grapes, but it wouldn’t be a summer blowout without a few local beer options. If you’re not vehement on vino, crack open cans from regional breweries including Heavy Seas, Calvert Brewing, and Honor Brewing—the Chantilly, Virginia-based company that has become known for its philosophy of dedicating tap handles to honor veterans and fallen soldiers. 

Baltimore Wine Festival
June 17. Canton Waterfront Park, 3001 Boston St. 12-7 p.m. $15-95. 410-409-7123. Calling all vino lovers. The third annual Baltimore Wine Festival is back with more than 160 vintages from around the world. Seasoned sommeliers and Franzia fanatics alike can stroll through Canton Waterfront Park and enjoy everything from rieslings to rosés, with gourmet food from more than 30 area eateries like The Local Oyster and Dooby’s, live music, cooking demos, and family fun along the harbor.

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Promenade: Baltimore
June 2-25. Single Carrot Theatre, 2600 N. Howard St. Thu.-Fri. 6:30 p.m., Sat.-Sun. 2 & 6:30 p.m. $30-35. 443-844-9253. All the city’s a stage in this new show from Single Carrot Theatre, now in its 10th year. As part of a “love letter to Baltimore,” audience members will board buses and explore city sites while actors create an immersive theatrical experience, fusing fantasy with the everyday.

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Flock of Dimes  
June 8. Ottobar, 2549 N. Howard St. 9 p.m. $14-16. 410-662-0069. It’s been nearly two years since Wye Oak lead singer Jenn Wasner left the city streets of Baltimore to live a simpler life in rural North Carolina. It was there, from a quiet bungalow in the Old North State, that Wasner wrote her first full-length release under her solo moniker, Flock of Dimes. Released last fall, If You See Me, Say Yes is an accomplished feat, connecting the past with the present through bright, buoyant rhythms and introspective melodies. For one night, hear Wasner back in her hometown to promote her beautiful new tracks like “Birthplace” and “Semaphore.” 

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Paul Simon
June 9. Merriweather Post Pavilion, 10475 Little Patuxent Pkwy., Columbia. 6 p.m. $55-175. 410-715-5550. After more than 10 years, Paul Simon graces the Baltimore region (this time, with Lilith Fair songstress Sarah McLachlan in tow). For one night only, expect enduring favorites from his classic albums—fingers crossed for “The Boy in the Bubble”—and new hits from his most recent release, Stranger to Stranger. We, indeed, are still crazy (for Paul Simon) after all these years.

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HonFest
June 10-11. 1002 W. 36th St. Sat. 11 a.m.-10 p.m., Sun. 12-6 p.m. There are few more truly “Bawlmer” celebrations than HonFest in Hampden. For the 24th year, don boas, beehives, and other 1960s garb to honor the blue-collar spirit and historic workingwomen of Baltimore. It’s a rite-of-passage block party with local food, lots of live music, and, of course, the contest for Baltimore’s best hon.

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Tour Dem Parks Hon
June 11. Druid Hill Park, 900 Druid Park Lake Dr. 7 a.m. $20-55. In the early days of summer, hit the pavement for this 15th annual bicycle tour of Baltimore’s local parks. With the wind in your hair, cycle through the city’s diverse neighborhoods and luscious green spaces and make new friends along the way. Best of all, there’s a post-ride barbecue with live jazz.

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Janet & Walter Sondheim Finalists Exhibition
June 17-Aug. 13. The Walters Art Museum, 600 N. Charles St. 10 a.m.-5 p.m. Free. 410-547-9000. Before Artscape kicks off in July, head to The Walters to get to know the winners of Baltimore’s most prestigious visual art award—including city native Kyle Tata and his mixed media work. 

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Baltimore Pride
June 17-18. Charles North & Station North. Locations & times vary. Free. For one weekend each year, the heart of Baltimore runs ROYGBIV. Follow the rainbow at the 42nd annual Baltimore Pride celebration, feting the city’s LGBTQ community with block parties, dance parties, the iconic high heel race, and a festive, float-filled parade. 

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John Legend
June 20. Merriweather Post Pavilion, 10475 Little Patuxent Pkwy., Columbia. 7:30 p.m. $59-499. 410-715-5550. With an adorable new baby, a shelf-load of awards (Hello, Oscar!), and a hilarious supermodel wife, John Legend is on quite the winning streak. Hear the R&B singer-songwriter and pianist do what he does best when he graces the Merriweather stage with hits like “Ordinary People,” tearjerkers like “All of Me,” and sounds from his latest album, Darkness and Light.

We prayed for heat all winter long, and now, with warm weather finally upon us, all we want is a little something to cool us down. With lots of vino varietals and cold craft brews in the Land of Pleasant Living, head to one of these festivals for local sips of summer spirits.

GREAT GRAPES WINE FESTIVAL
JUNE 6-7: Oregon Ridge Park, 13401 Beaver Dam Rd., Cockeysville. 12-6 p.m. Free-$56. 410-887-1818. At this alfresco day-drink, sample more than 30 Maryland wines in the great outdoors of Baltimore County, with live music and local vendors.

ANNAPOLIS ARTS, CRAFTS & WINE FESTIVAL
JUNE 6-7: Navy-Marine Corps Memorial Stadium, 550 Taylor Ave., Annapolis. Sat. 10 a.m.-6 p.m., Sun. 10 a.m.-5 p.m. Free-$30. 410-263-4012. Just a short stroll from the historic heart of Annapolis, shop fine arts, browse handmade crafts, and sip on Maryland wine at the Naval Academy stadium.

CHESAPEAKE CRAB & BEER FESTIVAL
JUNE 13: Rash Field, 201 Key Hwy. 11 a.m.-3 p.m., 5-9 p.m. $29-110. 410-396-7931. This second annual festival brings together Marylanders favorite things with more than 50 beers, wines, and spirits as well as all-you-can-eat crabs being offered six at a time per person. Plus there will be live music from slide guitarist The Sauce Boss and beach-themed tunes from Sons of Pirates.

RARE AND OBSCURE BEER FEST 2015
JUNE 19-21: Max’s Taphouse, 737 S. Broadway. 11-2 a.m. Free entrance. 410-675-6297. Head to the Fells Point beer palace for its annual celebration of scarce and unusual brews, with over 60 bottles and 70 drafts from around the globe.

FLYING DOG SUMMER SESSIONS
JUNE 20: Flying Dog Brewery, 4607 Wedgewood Blvd., Frederick. 6:30 p.m. $25. 301-694-7899. Kick off Flying Dog’s annual brewery concert series with chilled craft beers and Hurray for the Riff Raff, an up-and-coming, New Orleans-based Americana band with folk-blues undertones.

BALTIMORE WINE FEST
JUNE 20: Canton Waterfront Park, 3001 Boston St. 12-7 p.m. $38-75. 410-409-7123. At Baltimore’s inaugural wine festival, choose from dozens of vinos, snack on local gourmet bites, and listen to live music at the Canton Waterfront—also with a full bar and craft beer.

VINE REWIND
JUNE 20-21: Linganore Winecellars, 13601 Glissans Mill Rd., Mt. Airy. 11 a.m.-6 p.m. $22.50-30. 301-831-5889. At this ’70s, ’80s, and ’90s throwback weekend, take a winery tour, try new wines with a souvenir tasting glass, and hear live, retro jams by two different bands.