This year, the esteemed and long-standing cycling event will expand its footprint to include the District of Columbia. The weekend kicks off bright and early on Saturday, May 31, with the Amazon Armed Forces Cycling Classic’s Challenge Ride. The Challenge Ride offers a 21km closed course that welcomes cycling enthusiasts of all skill levels, and will now start and finish in the Nation’s Capital. You will enjoy the opportunity to ride against the backdrop of Washington, DC, and Arlington’s most iconic landmarks. Participants can aim for gold, silver, or bronze medals, awarded based on the number of laps completed during the three-hour event.The weekend’s activities also include two days of races, featuring the nation’s top Pro/Am men’s and women’s cycling teams. Saturday’s race will be held on a short, spectator friendly course in DC, utilizing the same start/finishing area as the Challenge Ride. On day two, the racing moved to Arlington, VA, for the 27th edition of the Clarendon Cup Pro/Am bike races. For more information, click here.

The Old Town Festival of Speed & Style, presented by Burke & Herbert Bank, celebrates its sixth year from 10:00 a.m. – 3:00 p.m. in Old Town Alexandria. This high-profile event features an impressive lineup of rare supercars and vintage motorcycles, a live fashion demonstration at noon, live music, family-friendly fun, and a judged car awards presentation. The Festival draws thousands of visitors, boosts local business, garners media attention, and donates all proceeds to local nonprofits: ALIVE!, Community Lodgings, and the National Breast Center Foundation. New this year: a special showcase of iconic Jaguar vehicles from the 1950s–1980s, plus sponsor activations and music from two local bands. Burke & Herbert Bank proudly returns as title sponsor for the fifth year, reinforcing its commitment to Alexandria and community impact. For more information, click here.

The DC area theater industry will gather at The Anthem for an unforgettable evening that includes a red carpet welcome, a three course dinner, and the Helen Hayes Awards ceremony. The Helen Hayes Awards is DC’s biggest night in theater. To purchase a ticket, click here.

The Loudoun Pride Festival is the largest Pride event in the Northern Virginia region bringing together over 5,000 participants and 150 businesses, non-profits, and community leaders for a day of celebration and acceptance. You're sure to find everything you love with tons of free family-friendly activities like axe throwing and splatter painting, all-day musical lineups including headliner The Lauren Reedy Experience, an expansive beer and wine garden featuring local vineyards and craft breweries, and so much more. Join them at the Gay-zebo for dance, self-defense, and yoga classes or shop from dozens of local crafters and local business! Get to know some of the most incredible nonprofit organizations improving the community and sample a little something from over a dozen local favorite food vendors. All for a $5 donation to support three incredible local nonprofit organizations serving the LGBTQ+ community. For more information, click here.

Join on Friday evenings at 6:00 p.m. this summer for live music at the corner of St. Elmo Ave. and Norfolk Ave. In order to drink alcoholic beverages at the Summer Concert Series, drinks must be purchased from their licensed partners, Rock Bottom Brewery and Olazzo. Please do not bring alcohol from home, or beer or wine purchased from local stores. For more information, click here.

Nick’s Riverside Grill is offering a variety of specials in celebration of the Kentucky Derby: Makers Mark Mint Julep  $15, Pulled Pork BBQ sandwich fries & slaw $15, BBQ Chicken Pizza - Ranch Dressing $15, BBQ Chicken wings - ranch dressing Celery & Carrots  $15

The Point DC is offering the following specials in celebration of The Kentucky Derby: Makers Mark Mint Julep  $15, Kentucky Gamblers Punch  $15 (woodford, tea, simple syrup, strawberry lemon mint), Derby Day Sangria (pinot grigio, makers mark, pineapple juice mint, Hot Brown (traditional open faced turkey sandwich) fries & Slaw $22, BBQ Bourbon Wings  $15, Kentucky Bourbon Balls (dessert) $10

Join ChurchKey as they celebrate the 10th anniversary of their good friends at Ocelot Brewing Company. On this special night, Founder Adrien Widman will be in house as they pour all 6 of Ocelot’s anniversary drafts!

Join Medina for a one-night only bar takeover featuring Speed Rack co-founders Ivy Mix & Lynnette Marrero! Ivy & Lynnette will be behind the bar mixing up drinks from their co-authored book of cocktails, “A Quick Drink.” In addition to the featured cocktail list, we'll be serving snacks and a full menu of wine, beer & non-alcoholic drinks. To make a reservation, click here.

Problem Child, the bar formerly known as Duke's Grocery Navy Yard, is hosting a Kentucky Derby Watch Party from 4:00 - 8:00 p.m., featuring $8 Mint Juleps, $8 Bourbon Sours, and $8 KentuckyMules. The race will be shown on multiple TVs with sound on, and Jell-O shots will be given to those dressed in Derby attire!