As we wrap up another summer, it’s time to wave goodbye to family pool days and cookouts in city parks and say hello to books and backpacks. With the first day of school fast approaching (August 25 for Baltimore City and Baltimore County Public Schools), these local community events—packed with fresh haircuts, classroom supplies, youth mentorship, and even a few laughs—are here to help your students step into the school year strong. Most are free and include giveaways, but be sure to check details to confirm times, locations, and registration requirements.
School Supply Drives
8/20: Agrihood Back-to-School Pop-Up Shop
Carnival vibes will meet community spirit at the weekly Agrihood Baltimore Farmers Market in Druid Hill Park, which is hosting this special event with the Northwest Wellness Project. Enjoy popcorn, cotton candy, water activities, face painting, and a moonbounce, plus local food vendors and fresh produce. Highlights of the community gathering will be free backpacks, school supplies, and haircuts to get students ready for the classroom. 3100 Swann Dr. 3:30–7:30 p.m.
8/20: Diversified Housing Back-to-School Backpack & School Supply Giveaway
Get ready for the school year with free backpacks and supplies at the Randallstown Community Center, sponsored by local housing agency Diversified Housing Development. Limit two bookbags per household; students must be present to receive them. 3505 Resource Dr., Randallstown. 4-7 p.m.
8/23: August Rose Health Center Back-to-School Backpack Giveaway
Glen Burnie’s August Rose Health Center will give away stuffed backpacks while supplies last. Music and Italian ice, plus parent giveaways, are also in store. 7477 Baltimore Annapolis Blvd, Glen Burnie. 11 a.m.–2 p.m.
8/30: Back-to-School Community Cookout & Backpack Giveaway
Head to the Baltimore City District Courthouse for an afternoon of food, music, and fun—plus free backpacks and school supplies—organized by the Baltimore City State’s Attorney’s Office’s Neighborhood Engagement & Safety Tour (N.E.S.T.). 1400 E. North Avenue, 12–4 p.m.
End-of-Summer Fun
8/20: St. Vincent de Paul of Baltimore Head Start Back-to-School Block Party
Cap off the summer fun with barbecue fare, snowballs, face painting, a moon bounce, supply giveaways, and more at St. Vincent de Paul’s Sacred Heart of Mary site in Southeast Baltimore. If you’re looking for early childhood education programs for your little ones, there will be opportunities to chat with Head Start teachers and even register on the spot. 6726 Youngstown Ave., Dundalk. 1-3 p.m.
8/22: Candiland Kickback 2 School Bash at Peabody Heights
Local treat purveyor The Cotton Candi Machine is hosting this family-friendly, end-of-summer bash at Peabody Heights Brewery. Swing by for free school supplies, music, face painting, caricature portraits, henna tattoos, pay-as-you-go pinball, $15 unlimited arcade play at The Dugout, and, of course, cotton candy. All adult beverage proceeds will support the brewery’s bathroom renovation fund. For more information, follow @cotton_candi_machine on Instagram. 401 E. 30th St. 4-8 p.m.
8/23: Ascending Back-to-School Fair
Head to the Weinberg Y in Waverly for an afternoon of back-to-school fun brought to you by local youth education nonprofit, The Ascend Project Corporation. Enjoy raffles, games, food vendors, free school supplies, and live music spun by DJ El Presidente. If that isn’t enough to get you excited—free access to the Y is included throughout the event. 900 E. 33rd St., 11 a.m.–3 p.m.
8/23: Mayor’s Back-to-School Kick-Off
Bring the whole family to War Memorial Plaza outside of City Hall for this annual event with Mayor Brandon Scott. There, you can not only soak up the final days of summer with live entertainment and local culinary treats, but you can also receive free backpacks, school supplies, and access to community resources like utility assistance and rental case management. 100 Holiday St., 11 a.m.–4 p.m.
Haircuts and Wellness
8/20: Fades, Braids, and Beyond in Poppleton
Kick off the school year with fresh haircuts and braids—sponsored by the United Way of Central Maryland—at the newly renovated Poppleton Recreation Center. The first 100 attendees get free ice cream. 1049 W. Saratoga St. 3-7 p.m.
8/22: Divine Counseling Back-to-School Fair
Hosted by Owings Mills-based mental health practice Divine Counseling, this event offers free haircuts, facials, waxing, shoes, uniforms, school supplies, and optional counseling and motivational support. Barbers, stylists, mentors, and volunteers are encouraged to join. 1133 Pennsylvania Ave., 3-8 p.m. To volunteer, DM @youaredivine_counseling or call 443-955-2662.
8/23: Back-to-School Haircuts by Kingdom Nation Church and Ministries
Send your young scholars back to school with confidence with free, first-come, first-served haircuts and braiding. Space is limited, so be sure to reserve early. For details, call 706-570-5288 or email admin@kingdomnationbmore.com 5300 Edmondson Ave. 9 a.m.-5 p.m.
8/23: Conscious Heads Barber Shop Free Haircut Event for Kids
Kids ages 6-12 can get a fresh cut—sponsored by Iota Phi Theta Fraternity—for the new school year from barber Ricardo Winchester at Conscious Heads in Old Goucher. Register at bluestandardgrooming.com. When booking an appointment use code: IOTA or BRANDON. Spaces are limited. 219 E. 25th St.
8/23: Back to School Open House
The Cortiva Institute—a wellness education school in Linthicum Heights—invites the community to this open house where students can receive free spa services to start the year off looking and feeling their best. (Think: mini facials, brow waxes, and chair massages.) There will also be free backpacks, face-painting, raffle prizes, and campus tours for anyone interested. 517 Progress Dr., Suite A-J, Linthicum Heights, 10 a.m.-3 p.m.
8/24: Back 2 Skool Cutz
Local caterer Kaylah’s Jumpin’ Out the Pot is serving up more than Southern fare this weekend. Young men and youth heading back to the classroom can claim a spot for a free haircut and refreshments. (Limit two per household.) Call 410-542-2158 to register. 3605 West Rogers Ave., 12-3 p.m.
Arts and Comedy
8/21: Lil’ Laughs Back-to-School Comedy Show at Baltimore Comedy Factory
Grab tickets now for this hilarious evening celebrating teachers, mentors, and youth professionals of all kinds hosted by Baltimore native comedian and advocate “Big Fred” Watkins. Ticket proceeds will support Lil’ Laughs, Watkins’ youth program that inspires confidence through laughter, specifically with after-school comedy clubs, anti-bullying and anti-violence assemblies, and other mentorship programs. Surprise guests will round out the show. 5625 O’Donnell St., 8 p.m. $30.
8/24: Laugh Back to School Comedy Show & Donation Drive at The Port Comedy Club
For one night, educators will take the stage and swap homework for hilarity at The Port in Fells Point. Be sure to bring a school supply donation for $2-off draft beers and mixed drinks. Proceeds from the 21-and-over show will support backpacks and supplies for students in need. 813 South Broadway. 4 p.m. $12.99
9/13: Back to School Intentional Vision Board Workshop at R. House
It’s never too late to start the school year with purpose. Join wellness coach Tamara “TeeKay” Kumoji at R. House in Remington for sessions on goal-setting, mindfulness, coping skills, and vision boarding—sponsored by Catonsville’s Kre8tive Kidz Boutique—to carry your best intentions through the year. 301 W. 29th St., 2-5 p.m. $17.85
If you’re able to gift supplies and looking for an ongoing donation drive, the Baltimore County Public Library will be collecting everything from crayons and colored pencils to folders, dividers, and three-ring binders at all of its 19 branches through September 13. More info, here.