Nothing is worse than a forgettable weekend! Instead of staying home on the couch, explore the beautiful DMV region with events across Maryland, DC, and Northern Virginia. Whether you’re an art aficionado, a certified beer drinker, or an eager foodie looking to sample small bites — there’s a little touch of something for everyone this Friday, Saturday, and Sunday.
Shows, Activities, Events & More in Maryland This Weekend
This weekend, Maryland has lots of fun events and activities on deck for you to enjoy. From the Frederick Festival of the Arts to the Food Truck Sunday Funday in Westminster, take advantage of delicious bites and original artwork!
Annual Reisterstown Beer & Wine Festival
Where? 54 Main Street, Reisterstown
When? June 7th
Get ready to raise a glass this weekend and sip, savor, and celebrate the annual Reisterstown Main Street Beer & Wine Festival this Saturday. The festival is scheduled from 12:00 PM to 5:00 PM and general admission tickets are on sale for $17.85. Kids ages 14 and under are free with an adult ticket holder. This is a family-friendly event, complete with food trucks, live music, artisan vendors, and much more. Festivities will be held rain or shine, so keep an eye on the forecast! Adults can take advantage of the multitude of showcased beverages at the festival from local wineries, breweries, and distilleries! This year’s lineup is Raven Beer, M8 Beer, Key Brewing, Roman Clarke Wines, Rosie Cheeks Distillery, and many more. Your glass will never be empty! Food trucks onsite will include Jimmy’s Famous Seafood and Taco Bar. Live music will be played by Harlan County Kings and Soul Magnets.
33rd Annual Old-Fashioned Strawberry Festival
Where? 3838 Nine Road, Finksburg
When? June 7th
Grab a group of friends and head to Messiah’s 33rd Annual Strawberry Festival on Saturday from 9:00 AM to 4:00 PM at the Gamber Volunteer Fire Department Carnival Grounds. Sample delicacies from the strawberry shortcake booth or participate in the silent auction for a chance to win exciting prizes. The festival will feature crafts, vendors, pony rides, hay wagon rides, entertainment and so much more. This year’s vendor lineup includes products such as artisan jewelry, paper crafts, native plants, candles, handbags, soap, and much more. Whether you’re shopping for something specific or you’re coming with an open mind, you’re sure to find something that strikes your fancy at the Strawberry Festival!
22 Miles to Break Boundaries Hero Run
Where? 2700 Riva Road, Annapolis
When? June 7th
Bring out the whole family for the community festival this Saturday from 10:00 AM to 2:00 PM at the Annapolis High School campus. There will be face painting, yard games, and an array of kids’ activities, as well as food trucks serving up local fare and vendor booths showcasing both local and veteran-owned businesses. If you want to stretch and unwind, check out the 10:00 AM yoga class (no registration required). The hero run is scheduled for 11:30 AM, with participants invited to walk, run, or cycle for a hero along the 2.2-mile course. Write your hero’s name on your bib to honor them throughout the race. Registration is required for race participation, though it’s free for military, veterans, and youth. There will also be a 33-mile challenge on Friday, June 6th, for those who want to face the ultimate challenge.
Frederick Festival of the Arts
Where? 50 Carroll Creek Way, Frederick
When? June 7th & 8th
The 31st Annual Frederick Festival of the Arts will be hosted at Carroll Creek Linear Park this Saturday and Sunday from 10:00 AM to 5:00 PM on both days. Admission is free and guests are invited to check out some of the region’s most talented artists during this unforgettable showcase. Whether you turn the Festival of the Arts into a day trip or you’re local to Frederick, you’ll appreciate the beautiful historic Downtown Frederick and the park’s urban charm and surrounding specialty shops, outdoor dining options, and local distilleries and breweries to grab a refreshing beverage of your choice. The festival will take place across two areas, with the second being the craft marketplace on Carroll Street.
Food Truck Sunday Funday
Where? 500 South Center Street, Westminster
When? June 8th
Food Truck Sunday Funday at the Carroll County Farm Museum is scheduled for 12:00 PM to 5:00 PM, with free admission and free parking for attendees! This is one of the largest free food truck events in the area, so swing by and grab something to eat with friends, family, and fellow community members. Food options will range from savory favorites to sweet treats, with live entertainment scheduled throughout the day to keep the vibes high. Participating food and drink vendors include The Crabby Pretzel, Cousins Maine Lobster, Macho Chicken, Ruhlman Brewery, Frosty Softy, and many more. Retail and shopping vendors such as Good Time Health, Bliss Face Painting, Tri Star Martial Arts, and others will also be in attendance.
Shows, Activities, Events & More in Washington D.C. This Weekend
The capital city is ringing in Pride month this June, with the WorldPride Parade and Taste of Pride curated menus across town. Take advantage of the first Saturday of the month at the National Gallery of Art and enjoy pop-up activities.
WorldPride Parade
Where? 14th Street & T Street, NW
When? June 7th
Catch the final act of WorldPride this weekend with the grand finale at the iconic Capital Pride Parade, which will honor the history and the evolution of the LGBTQ+ neighborhoods in Washington, DC. The parade is scheduled for a 2:00 PM step-off. There will be a post-parade concert and a family-friendly festival to follow. Check out the Camp Pride Family Area in John Marshall Park with the ultimate kids’ zone, complete with an interactive coloring installation and DIY crafts like friendship bracelets and bandana designs!
First Saturdays
Where? 4th Street & Constitution Avenue, NW
When? June 7th
Each month, families are invited to participate in First Saturday festivities at the National Gallery of Art. These festivities are designed to be a fun and relaxed experience that features art-making, films, and special pop-up activities. All activities are free, with most hosted on a first-come, first-served basis. Select activities may require registration, so plan ahead so you don’t miss out! June’s First Saturday events include hands-on activities in the Kids’ Play Space starting at 10:00 AM in the East Building’s Central Atrium, Drop-In Artmaking in the Atrium, and a Pop-Up Library from 11:00 AM to 3:00 PM in the Study Center. Make sure to check out some of the latest exhibitions, such as Little Beasts in the West Building!
Taste of Pride
Where? Various Locations
When? Through July 31st
Lace-up your shoes and get ready to embark on what’s sure to be a delectable culinary journey that’s running through the summer! Check out the highly anticipated Taste of Pride, which celebrates the LGBTQ+ community and the exquisite flavors found across the National Capital Region. Talented chefs and the area’s best restaurants will be curating special menus that showcase the best of their culinary artistry. This year’s Taste of Pride program is a collaboration between DC’s Business Improvement Districts over the course of multiple months to showcase distinctive flavors and culinary talents in the area’s most vibrant neighborhoods.
Shows, Activities, Events & More in Northern Virginia This Weekend
Make the most of your time off in NoVA this weekend, with the Saint Katherine’s Greek Festival in Falls Church or the Sunday Art in the Park event in Reston. Bring the pups out to the Paws on PenFed Plaza in Tysons, where you’ll find pet vendors galore ready to spoil Fido!
Saint Katherine’s Greek Festival
Where? 3149 Glen Carlyn Road, Falls Church
When? June 6th-8th
Join the Falls Church community for the 2025 Saint Katherine’s Greek Festival this weekend. The festivities will kick off Friday from 11:00 AM to 9:00 PM, with tasty Greek bites and pastries, live Greek music, and authentic Greek dancing all evening long. Saturday’s Taverna Greek Night is scheduled from 9:00 PM to 1:00 AM, so party extra late in their Small Hall with live music by the Palko Band and DJ Manolis. The late-night event will feature a cash bar and light hors d’oeuvres to keep you fueled. An entrance fee of $20 will be in effect and guests must be 18 and over.
Taste of Springfield
Where? 6500 Springfield Mall, Springfield
When? June 7th
The 8th annual Taste of Springfield Festival will be held in the parking lot near JCPenney & Dick’s Sporting Goods. This Saturday from 11:00 AM to 5:00 PM, enjoy a community celebration with good food, exhibitors, performances, and live music. This is a family-friendly festival, so bring the kids out to sample delicious bites from local restaurants and chefs. There will be entertainment for all ages, with the schedule featuring DJ Greg Mills from 11:00 AM To 5:00 PM, All Star Cheer at 12:00 PM, Suburban Gypsies at 1:15 PM, Hodges Fitness at 3:00 PM, N Tyme Jazz Ensemble at 4:00 PM and more! Participating food vendors at this year’s Taste of Springfield include Burnt Ends BBQ, Crabby Noodles, Day and Night Cereal Bar, Fantasy Cakes, The Vegan Factory, and lots more!
Fairfax City Pride Launch Event
Where? 3999 University Drive, Fairfax
When? June 7th
Ring in Pride Month this June with Fairfax City Pride! Everyone is welcome to participate and join in on the festivities. This Saturday from 9:30 AM to 11:30 AM, head to Old Town Hall for this Pride Launch Event in collaboration with community vendors from both George Mason University and the Northern Virginia area. There will be free children’s activities on the upper level of the town hall, as well as free caricatures, fairy hair, face painting, crafts, balloons, music, and much more. At approximately 10:00 AM, help representatives from the cities of Fairfax and Mason give a warm welcome to commemorate the start of Pride Month. There is no admission cost for this event! Circle June 23rd on your calendar for Funday Monday Storytime at the Fairfax City Regional Library for a Pride-themed story time and craft.
Paws on PenFed Plaza
Where? 1961 Chain Bridge Road, Tysons
When? June 7th
This Saturday, join fellow dog-loving community members at the Paws on PenFed Plaza. From 11:00 AM to 3:00 PM, bring your pups to the plaza for a full day of activities that celebrate furry friends. Hosted by PenFed Credit Union, this is an exciting opportunity to enjoy the dog park and cool off at the splash pad. There will be 20+ pet vendors in attendance, as well as the Woofbowl dog food truck and rescue dogs that are hoping to be adopted! Attending vendors include Bark and Boarding, Homeward Trails, First Steps Academy, and many more. The credit union will have an automatic treat machine, as well as a puppy pool, giveaways, and more. Make sure to snap a photo with your dog and turn them into an Instagram-worthy meme. Credit union members will also get a VIP gift when they show their PenFed card or a bank statement.
Sunday Art in the Park: Ellington’s Caravan
Where? 11900 Market Street, Reston
When? June 8th
This Sunday, enjoy a leisurely evening in Reston Town Square Park with the sounds of Ellington’s Caravan. This is a free event. Art in the Park is organized by the Reston Community Center. Feel free to pack a picnic and join the renowned Shenandoah Conservatory on recurring Sunday evenings throughout the summer for live jams. Ellington’s Caravan is a Duke Ellington Tribute band, so expect some of Ellington’s most beloved works, as well as some of his lesser-known treasures. In the case of inclement weather, this event may be canceled so keep an eye on the forecast!
We Hope You Enjoy Your Weekend!
Ready to kick off this weekend and make it one to remember? Hit the ground running on Friday and banish the Sunday scaries before they even have a chance to strike! From Art in the Park events, Pride month festivities, beer and wine festivals, and much more, the DMV region has something for you. Remember to visit us again next week so you know what the weekend itinerary looks like!