August is just around the corner, which means that summer is drawing to an end quickly. Preparing for back-to-school will be here before we know it. I put together a guide to highlight resources, and provides information for getting ready for the start of a new academic year.
INFORMATION BY COUNTY
Calvert County- The first day of school for Calvert County students is Tuesday, August 25, 2026. Be sure to check on their site for orientations, meet & greets, school supply lists and registration information here.
Charles County- The first day of school for Charles County students is Monday August 24, 2026. Be sure to check on their site for orientations, meet & greets, school supply lists and registration information here.
Prince Georges County- The first day of school for Charles County students is Tuesday, August 25, 2026. Be sure to check on their site for orientations, meet & greets, school supply lists and registration information here.
St. Mary’s County- The first day of school for Charles County students is Wednesday, August 26, 2026. Be sure to check on their site for orientations, meet & greets, school supply lists and registration information here.
BACK-TO-SCHOOL EVENTS & RESOURCES
MARYLAND TAX FREE WEEKDate: August 9-15, 2026
Location: Maryland
Details: The second Sunday of August through the following Saturday is designated as Shop Maryland Tax-Free Week each year. During this week, qualifying apparel and footwear priced at $100 or less per item are exempt from the state sales tax. The first $40 of a backpack or bookbag purchase is also tax-free.
BACK TO SCHOOL- CHURCH IN THE PARK
Date: August 1, 2026
Time: 10:00 AM
Location: Bensville Park- Waldorf, MD
BACK TO SCHOOL FIELD DAY
Date: Thursday, August 6, 2026
Time: 10:00 AM
Location: Dahlgren Base- Joy Park
Details: Summer’s winding down, so let’s send it off right! Join us for a morning packed with competitive games, music, food, activities, inflatables, prizes, back to school supplies, and more!
Cost: FREE
Registration: None
BACK TO SCHOOL PARTY
Date: Thursday, August 6, 2026
Time: 4:00 PM – 6:00 PM
Location: Indian Head FFR- Community Rec Center
Details: Join in a fun celebration with school supplies, food, games, and fun!
Cost: FREE
Registration: None
BACK TO SCHOOL EVENT
Date: Saturday, August 8, 2026
Time: 10:00 AM
Location: Sports & Wellness Complex parking lot (11170 Mall Cr. Waldorf, MD 20603)
Details: Join Commissioner Dr. Amanda Stewart for her annual Back to School Community Fiesta. The event will continue while supplies last. This is a drive through event that will include helpful information stops, healthy eating tips, local information and resources, and fun learning activities. This event is open to Charles County students in grades K-12, and the first 350 students will receive a backpack filled with supplies. Child must be present and accompanied by parent/guardian to receive a backpack. Acceptable forms of proof include: Parent Vue, last report card, or student ID from previous year.
Cost: FREE
Registration: None
BACK TO SCHOOL BASH
Date: Saturday, August 8, 2026
Time: 10:00 AM – 2:00 PM
Location: USBTA- 4450 Indian Head Rd. Indian Head, MD
Details: This FREE family-friendly event is open to the community and designed to help students start of the school year strong.
Cost: FREE
Registration: None
BACK 2 SCHOOL BASH
Date: Sunday, August 9, 2026
Time: 11:00 AM
Location: Tanger Outlets – Oxon Hill, MD
Details: Get ready for back-to-school fun at Tanger on Sunday, August 9th from 11AM–1PM! Our Back 2 School Bash, sponsored by Prince George’s Community Federal Credit Union, will take place at the playground, next to Columbia Factory Store. Bring the family out for face painting, balloon art, fun photo ops giveaways and more.
Cost: FREE
Registration: None
SCHOOL SUPPLY PROJECT
Date: Saturday, August 15, 2026
Time: 9:00AM-12:00PM
Location: New Life Church- 9690 Shepherd Creek Pl. La Plata, MD
Details: In need of a backpack and school supplies for the upcoming school year? Then stop on by! Must have proof of residency, and enrollment in CCPS or Homeschool.
Cost: FREE
Registration: None
SCHOOL SUPPLY PROJECT
Date: Saturday, August 15, 2026
Time: 10:00AM-12:00PM
Location: Waldorf Senior & Recreational Center, 90 Post Office Rd, Waldorf
Details: Get ready for the new school year! Join the Waldorf Senior & Recreational Center for our annual Bookbag Giveaway, where we’re helping students head back to school with confidence.
Cost: FREE
Registration: None
BACK TO SCHOOL FIELD DAY
Date: Saturday, August 15, 2026
Time: 11:00 AM – 3:00 PM
Location: Calvert County Baptist Church- 150 Ball Rd. St. Leonard, MD
ANNUAL COMMUNITY SUPPORT DAY
Date: Saturday, August 15, 2026
Time: 1:00 PM
Location: LCCM- 15522Livingston Rd. Accokeek, MD
Details: Join us for our Annual Community Day! Looking forward to seeing you there! This is event open to the public, registration is appreciated
Cost: FREE
Registration: RSVP Sign-Up Genius
BACK TO SCHOOL FIELD DAY
Date: Saturday, August 15, 2026
Time: 3:00 PM – 6:00 PM
Location: Calaway, MD
Details: As the cost of everything keeps rising, neighbors helping neighbors matters more than ever. Join us for our FREE Back-to-School Community Swap, where Southern Maryland families can share school supplies, clothing, and everyday essentials so every student starts the year with what they need.
Cost: FREE
Registration: RSVP Encouraged
BACK TO SCHOOL FIELD DAY
Date: Saturday, August 22, 2026
Time: 11:00 AM- 1:00 PM
Location: All American Steak House- Waldorf, MD
Details: Join us for our Annual Back to School Event, where you will find school supplies for all ages, clothes, cleaning and hygiene supplies, shelf-stable food, and more! All items are FREE while supplies last. Please bring your own bags.
Cost: FREE
Registration: RSVP Encouraged
EXTRA ARTICLES
Back to school can be a positive, or stressful experience; here is an extra articles to help with little ones dealing with back to school anxiety. Additionally, there is an article for those considering homeschool and not sure of where to start.***The Playful Parent is a 501(C)(3) Non-profit created to advocate learning through play, and promote family bonding. All content is intellectual property of TPP, and information shared is to help provide a non-biased resource for families. If you have questions about programs or events be sure to contact the business directly. The Playful Parent isn’t affiliated with any of the schools or events.***
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