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The Upperville Colt & Horse Show: Monday, June 5 (Image: Teresa Ramsay)

Out and About: Horses, comedians & ice cream -- oh my!

Monday, June 5

The Upperville Colt & Horse Show: The Upperville Colt & Horse Show returns on June 5-11 for its 164th year. The oldest horse show in the country was founded in 1853 to encourage better breeding of horses. Since that time, thousands of equestrians, horse breeders and spectators have gathered in Upperville each year to admire some of the nation’s most talented horses and riders. Grafton Farm, 8600 John S Mosby Hwy, Upperville, VA 20184, gates open at 8 a.m. daily, $10 per day

A Night of Laughter and Song: A star-studded lineup of celebrities and artists will perform in support of veterans and at-risk youth. Begun in 2005, the David Lynch Foundation's Center for Health and Wellness works to heal traumatic stress and transform the lives of at-risk populations, both youth and adult. The one-night only event features appearances by Jerry Seinfeld, Hugh Jackman, Jay Leno, Katie Couric, Margaret Cho, Deborra-lee Furness, Kesha, Ben Folds, Angelique Kidjo, and Sharon Isbin. Kennedy Center, 2700 F St. NW, 8 p.m., $69-$149

Tuesday, June 6

Pop-Up Magazine Spring Issue: What happens when your favorite writers, artists, radio producers and an orchestra make a live show together? Pop-Up Magazine! These multimedia storytelling events aren’t recorded, so you have to be there to see it. This tour’s lineup includes Washington Post columnist Alexandra Petri, This American Life producer Karen Duffin, chef Samin Nosrat, comedian Yassir Lester (Girls, The Carmichael Show), MAGIK MAGIK orchestra, and more. The Lincoln Theatre, 1215 U St NW, 7:30 p.m. $30

Wednesday, June 7

Dine-N-Dash: 30 restaurants, three featured chefs and countless hours of live music combine to create one huge night. With five to eight dishes and four drinks at each restaurant, you won't go hungry. Roaming waitstaff and food stations at each location will keep traffic moving, so no need to worry about lines, wait times, or ordering. Enjoy unlimited food and drink at all participating restaurants until you're full, or the event ends -- whichever comes first! And don't miss a chance to rub elbows with Chef Jose Andres, Andrew Zimmern, and Ted Allen. All proceeds benefit World Central Kitchen. Can start your tour at various restaurants, 6 p.m., $125-$400

From Kennedy to Obama -- A Conversation with White House Photographers: A White House photographer has special access to what happens at “The People’s House,” from carefully orchestrated official events to the daily life of the First Family. Join celebrated White House photographers Dennis Brack, Sharon Farmer, and Diana Walker as they share their images and the stories behind them. The conversation is moderated by Lawrence Schiller, a former LIFE magazine photojournalist who organized the exhibition American Visionary: John F. Kennedy’s Life and Times. Smithsonian American Art Museum, F and 8th St. NW, 6:30 p.m., free

Dinner Unplugged: Exhausted from your over-committed schedule and increasingly fast-paced, go-go-go lifestyle? Detox from the nonstop technology mid-week with this recurring Wednesday night dinner – sans smartphones. Enjoy a laid-back and alternative experience, power off your phone, and unplug with good old-fashioned conversation over a delicious meal from Shouk. BYOB and get some IRL face time with new people over games, conversation starters, and more. Sixth & I, 600 I St. NW, 6 p.m., $12

Thursday, June 8

Ice Cream Jubilee Tasting: Ice Cream Jubilee is welcoming summer with six new flavors. Join them for an advance tasting of these flavors before they're revealed to the general public. Two favorites from last summer are returning and four brand new flavors -- savory, spicy, salty, and sweet -- will be debuted. Your ticket grants you entrance to this private event and lets you take home a pint at the end of the night. Ice Cream Jubilee, 1407 T St. NW, 5 p.m., $12

Cider Tasting ad Grilled Cheese Bar: Unwind and celebrate the start of summer at a gourmet make-your-own grilled cheese bar followed by a guided cider tasting with Cider Historian, Michael Stein. This curated tasting features cider from Blue Bee Cider, Virginia’s first urban cidery. Sixth & I, 600 I St.NW, 7 p.m., $15

Laverne Cox in DC: Madame Tussauds Washington, D.C. is celebrating 10 Years on F Street this summer with exciting new wax figures never seen before in D.C., and in town for a limited time only. The attraction is celebrating Capital Pride by welcoming the figure of Orange Is The New Black star, Laverne Cox. She is the first-ever transgender figure to be created by Madame Tussauds in its 250-year history—originally launched out of Madame Tussauds San Francisco. The figure is styled in the dress she wore for her iconic 2014 TIME Magazine cover. Ms. Cox ‘s figure will be in the attraction from June 8-11. Madame Tussauds, 1001 F St. NW, open from 10 a.m. to 6 p.m. daily, $22