Author: The Playful Parent

The Playful Parent was created in 2016 as a blog to share the joys and craziness of parenting. The founder of The Playful Parent is a full time domestic energizer and has a Bachelors from Marymount University and a Masters in Clinical Counseling from Johns Hopkins University.

2026 MARYLAND FALL GUIDE: PUMPKIN PATCHES, FARMS AND FALL FESTIVALS

September has arrived, and fall officially begins in just a few short weeks; which means it’s time to start planning those classic autumn adventures! From picking the perfect pumpkin, or wandering through apple orchards to getting lost in a corn maze, there area  a handful of local farms that offer so many fun ways for families to celebrate the season.

Over the past several years, our family has traveled near and far to visit farms, fall festivals, pumpkin patches, orchards, and more. Along the way, we’ve learned what makes each destination unique, what families can expect when they visit, and which experiences are worth adding to your fall bucket list. I’ve taken all of that knowledge and experience and put it together in this guide to help Maryland families and those visiting from beyond plan a memorable fall adventure during the 2026 season.

In addition to this guide, you’ll find links to individual guides for each farm, where I share more details about what to expect, things to know before you go, and tips to help you make the most of your visit. I hope this guide makes planning your family’s fall outings a little easier—and inspires you to discover a new favorite farm along the way! Happy fall, and enjoy!

CALVERT COUNTY

HORSMON FARM

  • Location: 1865 Horsmon Farm Ln. St. Leonard, MD
  • Phone: 443-532-5761
  • Website: www.horsmonfarm.com
  • Information: Horsmon Farm fall festival will celebrate their opening weekend September 19 & 20, 2026, and will run through November 1, 2026 this season. Fall festivities includes: pick your own pumpkin patch, wagon ride, corn maze, farm animals, farm trail, corn pit, sand pit with dirt diggers, tug-o-war and hop balls. Don’t forget to check out their website for special events each weekend including; scarecrow making, tractor weekend and more. If you are looking for a place to pick up beautiful flowers this is the place, their mums are gorgeous and home grown. Purchase your tickets in advanced online. Hours are Fridays 11AM-5PM, Saturdays & Sundays 10AM-5PM and weekday fieldtrips by reservation. Admission is $15 Kids (with small pumpkin) / $12 Adult/FREE Ages 2 and under. 10% discount offered to larger families of four or more, first responders and military.
  • Playful Parent Guide: Horsmon Playful Parent Guide Link 

JACK’S PRODUCE & LINDA’S GREENHOUSE

  • Location: 2925 Yoes Corner Rd. Port Republic, MD
  • Phone: 443- 295-8634
  • Website: www.jakesproducemd.com
  • Information: Jacks Produce is open weekends September – November from 9AM-5PM. In the fall, take a stroll through the pumpkin patch as you stop to pick up your produce. There are pumpkins of all shapes, sizes, and colors; there is something for everyone. Corn maze, corn pit, wagon rides and more available. Admission is $5 per person/2 and under FREE.

ROLLING ACRES FARM

  • Location: 3305 St. Leonard Road Port Republic, MD 20676
  • Phone: 443-532-7891
  • Website: www.myrollingacresfarm.com
  • Information: Rolling Hills Farm opening weekend is September – November 2026. Rolling Acres is open daily Monday-Saturday 10AM-6PM and Sunday’s 10AM-4PM. Activities include: maze, petting zoo, jumbo jump pillow, pumpkin patch, petal cars, tire mountain and corn pit.  Admission is $12 per person/FREE Ages 2 and under/ Families of 4 or more $10 per person.
  • Rolling Acres Playful Parent Guide Link

SPIDER HALL

  • Location: 3915 Hallowing Point Rd, Prince Frederick
  • Phone: 410-610-0094
  • Website: www.facebook.com/SpiderHallFarm
  • Information: Exciting news…Spider Hall is open on weekends the 2026 Fall season through out October. They have not posted a schedule or information yet. Activities include: hayrides, sorghum maze, jump pad, pick your own pumpkins and more! Stay tuned for details coming soon. This farm usually hosts great events such as movie nights, tractor treat and apple day.  Admission $12 per person/ 2 and under FREE.
  • Spider Hall Playful Parent Guide

CHARLES COUNTY

POP POP’S GREENHOUSE

***Update: Fall Festivities Closed this year***

SERENITY FARM 

  • Location: 6932 Serenity Farm Rd. Benedict, MD
  • Phone: (301) 399-1634
  • Website: https://serenityfarmatbenedict.com
  • Information: Every fall, Serenity Farm hosts for their annual Harvest Day weekend, a chance to come and pick a pumpkin, take a hayride, and interact with adorable animals in the Petting Farm! Please check their 2026 calendar for updates, they haven’t announced their schedule yet. Last years prices were $15 per person, 4 and under are admitted for FREE. Ticket price includes: pumpkin, petting pen, and hayride. Harvest House is open with apples, pumpkins, apple cider, mulling spices, and apple butter and many fall items. Weather dependent.

SHLAGEL FARMS

  • Location: 12850 Shlagel Rd. Waldorf MD 20601
  • Phone: (301) 645-4554
  • Website: www.shlagelfarms.com
  • Information: Shlagel Farms is open for general admission on the weekends through out the month of October during the hours 10 AM – 5 PM. Call to schedule field trips and private groups with availability Monday through Friday by appointment.  Admission was listed last year and not updated yet at $11 per person, children ages 2 and under are free. Shlagel farm is quaint, and more of a educational farm for fieldtrips or spot to simply pick a pumpkin; offerings are limited to wagon rides, petting zoo, and pumpkin patch.

ZEKIAH FARMS

  • Location: 5235 Bryantown Rd, Waldorf, MD
  • Phone: (240) 216-4065
  • Website: ww.zekiahfarms3.com
  • Information: Zekiah Farms is well known for their market that sells organic meat, fresh produce and local honey. This year they will be hosting a Fall Festival on October 3, 2026 10AM-4PM with live music, food trucks and lots of fun activities. Admission is FREE to all.
  • Event Link

ST MARY’S COUNTY

BOWLES FARM

  • Location: 22880 Budd’s Creek Rd. Clements, MD
  • Phone: 301-475-2139
  • Website: www.bowlesfarms.com
  • Information: Bowles Farm annual fall festivities will be open on weekends starting September 26, 2026 thru October 321, 2026. Hours of operation are Saturdays 10AM-6PM and Sundays 10AM-5PM. Friday’s are available for fieldtrips by appointment, group rate applies. Admission is $15 per person, free for children ages 3 and younger, $13 for groups of 15 or more. Kids of all age will enjoy the amazing corn maze, pumpkin patch, straw jumping pit, children’s play area, wagon rides and more. Be sure to check out their calendar for amazing events such as tractor races and more.
  • Bowles Playful Parent Guide

FORREST HALL FARM AND ORCHARD

T AND A FARM 

  • Location: 18281 St. Jerome’s Neck Rd, Dameron
  • Phone: 301-872-5003
  • Website: T and A Farm
  • Information: No new information posted yet. Last year activities included: pumpkin patch, hay maze, wagon rides, farm animals, play area and more. Be sure to check their page for family fun events.

PRINCE GEORGE’S COUNTY

MONTPELIER FARMS

  • Location: 1720 North Crain Highway, Upper Marlboro, MD
  • Phone: 410-320-0464
  • Website: www.montpelierfarms.com
  • Information: Montpelier Farms  Fall Festival will run September 12-November 8, 2026. September hours Saturday 10AM-9PM/Sunday 10AM-6PM. October hours Friday 5PM-11PM/Saturday 10AM-11PM/Sunday10AM-7PM. Weekday Play  Tuesday-Thursday 1PM-3PM. November Saturday 10AM-9PM/Sunday 10AM-6PM.  Admissions prices are Weekend- $19.95 per person (online), Weekday discount available, Kids 2 and under are Free! Fall Festival activities include: 7 acre corn maze, “Jack and the Beanstalk” corn maze, hay rides, petting zoo, pedal karts, cow belly bounce house, pumpkin bounce house, hay & play, kiddie corral, corn tepee, roping range, farm football lounge, “Spookley the square pumpkin” movie screening and bonfires. You add experiences on to your admission including: super mega slide, duck races, animal feed and giant bounce pillow.
  • Montpelier Farm Playful Parent Guide

MILLER FARM

  • Location: 10140 Piscataway Rd, Clinton, MD 20735
  • Phone: 301-297-9370
  • Website: www.millerfarms.com
  • Information: Miller Farms is a 267 acre farm located in Prince George’s County, Maryland, that has been family owned and operated since 1879. Miller Farm is known for their ice cream and lovely market open year-round. Fall festivities begin the weekend of October 3, 2026. Hours are Saturday’s and Sunday’s 10AM– 5PM. Tickets will be sold online only!!! ($14.95 per person, Free ages 24 months and under.) Weekday (Wednesday-Friday) fieldtrips can be booked online here.
  • Miller Farm – Playful Parent Guide

BEYOND

The following farms are beyond Southern Maryland; however, are hands down the BEST farms that we have visited! You won’t want to miss traveling beyond to celebrate fall at any of these farms, I promise!

CHERRY CREST FARM

  • Location: 150 Cherry Hill Rd. Strasburg, PA
  • Phone: 1-866-546-1799
  • Website: www.cherrycrestfarm.com
  • Information: Cherry Crest was the first farm we ever visited as a family, and is still our favorite farm of all time! Nestled right in the heart of Pennsylvania Dutch Land; this working farm is the perfect place to harvest family fun. It’s an added bonus that the Pennsylvania Railway runs through the property. You can ride the train to the farm or just enjoy watching the locomotive travel by. This year 2026 season they are open most Thursdays, Fridays and Saturdays September 19th through November 7, 2026. With over 50 different activities, it’s almost impossible to see and do everything in one day. My favorite activities for the toddler and preschool aged kiddos is Sprout Ville a tiny town play area, Little Wagon Express and Corn Barn. Favorite activities for school age kids include: Life Size Lincoln Log Cabin Building, Giant Jumping Pillows and Feed Mill a obstacle course for kids. Favorite big kid activities include tractor pull, Apple Blaster Canons, paint ball range and Corny Ball Cade. Favorite family activities include Farm Tour wagon ride, Country Road Carts and Flash Light Adventure Maze.
  • Cherry Crest Playful Parent Guide

BELVEDERE PLANTATION

  • Location: 1410 Belvedere Dr. Fredericksburg, VA 22408
  • Phone: 540-373-4478
  • Website: www.belvedereplantation.com
  • Information: Belvedere Plantation is a 645 acre heritage farm, built in the 1760s on the historic Rappahannock River near Fredericksburg, Virginia. You are sure to have hours of fun with attractions like a zipline, straw jump, trike track, pumpkin mountain slide, pedal carts, barrel train and jumping pillow. Check out their website for information on events like the Final Flashlight Maze and Pumpkin Pounding Event. Their 2026 season starts September 12th and runs through November 7, 2026. They are open most days Thursday thru Sunday weather contingent. Hours: Thursday & Friday Mornings 10AM-2PM/Friday Evenings 6PM-10PM/ Saturdays 10AM-10PM/Sundays 10AM-6PM/Columbus Day 10AM-6PM. Admission: $17.95-September/$19.95 October (Online Weekdays) and $23.95-September/$26.95 October (Online Weekdays). Tickets purchased at the gate are $5 more.
  • Belvedere Plantation-Playful Parent Guide

COX FARM  

  • Location: 15621 Braddock Rd Centreville, VA
    Phone: 703-830-4121
  • Website: www.coxfarmsva.com
  • Information: Cox Farm Fall Festival was closed last year, so I’m happy to announce they are back in business! The Fall Festival is open September 19, 2026 through November 9, 2026. The festival is open 10AM to 6PM through October, and 10AM to 5PM November. With a map full of outdoor activities, goat village, and Cornundrum Cornfield Adventure you will need more than one visit to see and do everything. This farm features the awesome six lane wide, 150 foot long dinosaur of a slide. Be sure to check out their website for events and live entertainment schedule. Check out their calendar for prices. Discount days as low as $15 per person and peak time tickets $30 per person.
  • Cox Farm Playful Parent Guide

GREENSTREET GARDEN

SUMMER FARM

  • Location: 7503 Hollow Rd. Middletown, MD 21769
  • Website: Summers Farm
  • Information: Summers Farm is located in Frederick, Maryland. Summers Farm opens September 5, 2026.  This year with an old-fashioned Harvest Festival featuring a Corn Maze, Pumpkin Patch, more than 30 activities, live weekend music, apple blasting and finger-lickin’ good food. Check out their calendar for fireworks and events schedule. This is a huge farm has a lot of fun activities.
  • Summers Farm Playful Parent Guide

CARNIVALS & FAIRS

MARYLAND RENAISSANCE FESTIVAL

  • Date: Saturday’s & Sunday’s August 29 -October 25, 2026  (Weekend Only) 10AM-7PM
  • Location:  Maryland Renaissance Festival – 1821 Crownsville Road, Annapolis, MD 21401
  • Details: Every one of the nine weekends of the Maryland Renaissance Festival is filled with more than 200 performers entertaining on ten stages, joust tournament field and streets of the 16th century English village. Seven weekends include additional performers or special guests to create additional themed Special Event Weekends.
  • PLAYFUL PARENT RENN FEST GUIDE

CHARLES COUNTY FAIR

  • Location: 8440 Fairground Road La Plata, MD
    Date: September 17-20, 2026
  • Information: FREE Parking on-site and at the satellite location at the Government building in La Plata. Thursday- Ride All Evening For One Price. Friday- “Kids Day” All Rides Reduced From 10:00 AM – 5:00 PM. Sunday- Ride 11:00 AM – 6:00 PM For One Price. Cost: Age 11 and over: $10/ Age 10 and under:  Free/ 4 Day Passes: $25.00. All School Children admitted FREE on Friday, September 15th from 9:00AM to 5:00PM. New this year all minors must be accompanied by a chaperone at least 21 years of age.
  • Charles County Fair Link

ST MARY’S COUNTY FAIR

  • Date: September 24-27, 2026
  • Location: 42455 Fairgrounds Rd, Leonardtown, MD 20650
  • Cost: $Daily: Adult ticket $7, children 6 to 12 $1, children under 6 free
  • Season passes: Adult $10, children 6 to 12 $2. Daily Deals: The rides take from 1 to 5 Carnival tickets. Carnival tickets cost $1 or a strip of 25 tickets costs $20. Friday (kids day) 10:00AM to 5 PM, all rides are 1 ticket (children only). Thursday and Sunday, wristbands are available for $30.  ($5 discount coupon is available at schools, and on-line Click here for coupon)
  • St. Mary’s County Fair Link

CALVERT COUNTY FAIR

  • Date: September 30- October 3, 2026
  • Location: 140 Calvert Fair Drive, Prince Frederick, MD 20678
  • Information: Cost- $5
  • Calvert County Fair Link

FOR MORE FALL FUN SEE THE FALL FESTIVITIES AND HALLOWEEN HAPPENINGS GUIDE- LINK!

***The Playful Parent is 501(c)(3) non-profit dedicated to providing free resources to the community that advocate learning through play, and promote family bonding. All information and photographs provided are intellectual property of TPP.***

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NATIONAL CHILDREN’S MUSEUM: PLAYFUL PARENT GUIDE

If you haven’t had a chance to visit the National Children’s Museum in DC yet, I highly recommend it. This museum is a wonderful place for developing young minds and curious young learners to learn and grow through interactive and engaging exhibits. Here’s a guide to help families prepare for a fun day at the museum.

STAY AND PLAY- EXHIBITS YOU WONT WANT TO MISS

DREAM MACHINE & LITTLE DREAMERS

When entering the National Children’s Museum, the first thing you will be greeted by is the Dream Machine. This massive indoor playground is the perfect spot for kiddos to put their gross motor and analytical thinking skills to the test as they navigate through an elaborate play structure. This section has a fun, warm and inviting sky theme with cloud climbers, floating cumulus seesaws, bubble maker, and a huge three-story climber and slide. While the larger play space is designed for children ages five and older, there is also a gated section dedicated for little ones to have a safe space perfect for their size to play in.  Little Dreamers is designed for infants and toddlers ages three and under. An adorable aviation theme provides music and texture sensory wall stations, a hot air balloon, and a climb on an airplane.

WEATHER WORLD & CLIMATE ACTION HERO

Climb into a world of weather where you can control the weather with a little magic (and green screen technology). Dance, make silly faces, and control the weather with a simple swish of the hand. Watch as your movements trigger weather phenomena ranging from rain and snow to blizzards and tornados. Be a hero by taking the action chart quiz, and discover how you can make climate changes in your home town.

ART & TECH SECTION

National Children Museum and Nickelodeon have teamed up to provide the Art + Tech exhibit which features a PAW Patrol Training Academy and Sponge Bob. Lights, camera, ocean! Use various light and shadow elements and life sized character silhouette’s to create scenes. Climb inside Spongebob’s giant pineapple house and watch the animations come to life. Paw Patrol fans will love this section, gather your crew and start the rescue! Build with Rubble, Explore wind with Skye and put out faux fires with Marshall. Before moving on to the next area make your way through “It’s about Slime.” A green slime themed sensory path. No worries, its mess free.

DATA SCIENCE ALLEY

In this section young minds can see how collecting data can be fun. Explore statistics by stepping through a colorful, reactive gateways to input data, send color coded pom-poms through wind-powered tubes that show a visual of how process data points work.

PLACITA MAGICA

Explore how engineering and architecture come together. Use problem solving skills to make and test out your own spiny top, build your own city maze and navigate a ball through it, and launch water droplets with moving air blowers in the Bernoulli fountain.

ENGINNERING AND GAMES

This section is where you will find activities that even the adults will enjoy. Shoot a basketball using a wind canon! Score a home run and practice throwing the perfect pitch by taking aim at drums and cymbals to strike a note! Put your engineering skills to test at the flight zone, where you can make and launch the perfect plane. Design, build, and race cars down a giant, adjustable custom race track! Learners observe how ramp height changes the potential energy, kinetic energy, and the force of gravity as they test their cars on adjustable ramps.

LITTLE MOVERS

Through project free-movement this space is provided to help infants and toddlers build fine and gross motor skills. Little movers has a soft padded flooring with plenty of space to move, jump, and crawl.

TINKERING CORNER

The Tinkering Corner is space that fosters creativity and imagination. Little ones can build upon the skills they have learned in the Museum and put them in action to design, create, build, and play with recycled and artistic materials.

VISITING EXHIBIT HALL

Visiting exhibits rotate seasonally, the current display in this room is Curious George, Let’s Get Curious. Be sure to check out this exhibit before it’s gone, this exhibit will be available until September 7. The next exhibit is Dinosaurs and will make it’s debut this Fall of 2026! Step inside the world of Curious George with scenes from the movie that are interactive.  There is a lot of opportunities for imaginative play in this section where you will find an immersive market, construction site, and farm.

PLAN LIKE A PRO- THINGS TO KNOW BEFORE YOU

Here are a few tips to help you plan like a pro. Let’s cover what to pack, where to park and everything in between.

  • First off- ticketing! You must purchase admission in advanced. Even if you have a membership you still need to make a time reservation. Tickets are digital and can be printed, or even added to your phones digital wallet to save time. Keep in mind that all adults must be accompanied by a child (age 0-12) for safety reasons. Tickets are also time stamped, so try to be as close to your scheduled time entry as possible. Don’t worry if you get caught in traffic, or are behind schedule they are usually flexible.
  • There are a variety of parking options around the area. Street parking is limited during tourist season. I recommend utilizing the parking garage in the Ronald Regan Building, which is only $19 for the entire day on weekends and holidays, and $20 for two hours on weekdays. You can also take the metro, the Federal Triangle stop we put you within steps on the museum.
  • Know where to go, be aware of where the restrooms are located just in case of emergencies. Bathrooms are located on the lower level near the Tinkering Corner. The facilities are kept extremely clean. They have three family stalls and gendered restrooms.  Baby changing stations can be found in the family stalls. There are also quiet rooms, and a nursing room on campus near the Little Dreamers Exhibit. You’re welcome to bring snacks and lunches into the Museum.
  • Snack attack- We all know little ones enjoy a mid-day snack. You can bring your own snacks to enjoy, or purchase snacks at Timgad Café attached to the Museum.
  • Share love, not germs- The museum does an excellent job providing hand sanitizer stations. I had my kids sanitize their hands through out the day, and wash their hands in the bathroom at the end of the day.
  • Wheels- The museum is fully ADA accessible with elevators, and inclusive exhibits. Additionally, there is stroller parking at the entrance of the museum. To keep walk ways clear it is recommended to park your stroller to cause congestion.

MUSEUM INFORMATION

Address: 1300 Pennsylvania Ave. NW, Washington, DC 20004

Hours: Open Wednesday-Monday 9:30AM – 4:30PM ***CLOSED TUESDAY’S***

Cost: Adults and Children 1 and over: $18.95 / Children under 1: FREE

Website: www.nationalchildrensmuseum.org

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BACK TO SCHOOL: 2026 SOMD GUIDE

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 WEEK
Date: 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
Details: Back to school event, all are welcome.
Cost: FREE
Registration: None
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
Details: School supply giveaway, food, games, raffles and more.
Cost: FREE
Registration: None
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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VALENTINES DAY IN SOMD MARYLAND

Here are a few ideas for making Valentine’s Day fun for the entire family. From our family to yours; we wish you a Happy Valentine’s Day! 

ScreenshotVALENTINES DAY -FAMILY NIGHT

  • Date: February 10, 2026
  • Time: 5:00 PM – 7:00 PM
  • Location: Silver Diner- Waldorf, MD
  • Details: Enjoy a family dinner and complimentary family photos.
  • Link

DADDY DAUGHTER DATE NIGHT

Date: February 11, 2026

Time: 5:00PM-7:00PM

Location: Chick-fil-A- California, MD

Details: Dads, it’s time for a special night out with your girl! Join us for Daddy–Daughter Date Night on February 11 from 5:00–7:00 PM at Chick-fil-A First Colony Center. Enjoy quality time, great food, and sweet memories you’ll both treasure!

Link

PIZZA WITH PARENTS

  • Date: February 12, 2026
  • Time: 5:00PM- 8:00PM
  • Location: Boston Pizza- Waldorf, MD
  • Details: Who’s ready for Pizza with Parents? ( formerly known as Daddy Daughter Dinner) Looking for a place to take your kiddos out for a pre valentines date night? Thursday, February 12 from 5:00 PM to 8:00 PM. Call to make your reservation we are very limited on seats available for this event!
  • Link

SNEAKER BALL DANCE

  • Date: February 13, 2026
  • Time: 6:00 PM – 7:30 PM
  • Location: Dr. Brown Elementary School- University Dr. Waldorf ,MD
  • Details: This PTO sponsored event sounds like a lot of fun. Cupid called- he wants YOU on the dance floor! Come on and dance your heart out to an encore of DJ.
  • Link

SWEETHEARTS PRESCHOOL PROM

  • Date: February 13, 2026
  • Time: 6:30PM- 8:30PM
  • Location: Somers Community Center
  • Details: Join us for a night to remember with your little sweetheart at Sweetheart’s Pre-K Prom on February 13! Begin your night with a red carpet entrance, followed by an evening of dancing, games, and light refreshments!
  • Link

VALENTINE’S DAY PAINT PARTY

  • Date: February 14, 2026
  • Time: 11:00AM
  • Location: Joyful Studio- La Plata, MD
  • Details: Celebrate Valentine’s Day with an easy-going, fun painting session! Join us for a fun-filled, relaxing moment of creativity to celebrate Valentine’s Day! With this Instructor-led painting session, you’ll receive painting materials and one canvas!
  • Link

VALENTINE SKATE

  • Date: February 14, 2026
  • Time: 12:30 PM – 1:50 PM
  • Location: Capital Clubhouse- Waldorf, MD
  • Details:
  • FSCSM invites you to join us at Capital Clubhouse for a Valentine’s Day Sweetheart Skate! During the event, the FSCSM Junior Board will be on site with a fundraising table.
  • ♥️ Bring your loved ones, friends, and family for a fun day on the ice
    ♥️ Stop by the FSCSM Junior Board fundraising table to pick up something sweet for your Valentine
    ♥️ Support Junior Board activities and leadership opportunities
  • We can’t wait to celebrate with you!
  • Link

VALENTINE’S DAY ICEDREAM SOCIAL

  • Date: February 14, 2026
  • Time: 4:00PM- 6:00PM
  • Location: Chick-fil-A- La Plata, MD
  • Details: Join us for dinner and enjoy a complimentary kids IceDream® cup—just our way of adding a little extra joy to your evening. This event is perfect for babysitters, grandparents, or anyone spending the evening with littles while parents enjoy a date night. And for our students and high schoolers—it’s a fun, affordable way to take someone special out for a sweet and simple dinner date. Our IceDream® cups can be topped with Chick-fil-A® favorites like chocolate chunk cookie pieces, brownie, Hershey’s® chocolate syrup, Oreo® crumbs, and cherries.
  • Link

VALENTINE’S DAY PARENTS NIGHT OUT

  • Date: February 14, 2026
  • Time: 6:00PM- 9:00PM
  • Location: My Gym- Waldorf, MD
  • Details: Event for kids ages: 3yrs 6mos to 10yrs. REGISTER: https://www.mygym.com/waldorf/events
    Kids’ Night Out Drop-Off event: Kiddos will be mixing love potions, growing crystal hearts, making glow valentine cards, and more Fun themed Activities includes: Chemistry Love Potions, Make Glow Hearts, Ninja Obstacle Courses, Games, Relays & Zip Line, PLUS Pizza & Movie.
  • Link

VALENTINE’S MAKERS MARKET- DEFROSTED EDITION

  • Date: March 14, 2026
  • Time: 9:00AM- 2:00PM
  • Location: Annmarie Gardens
  • Details: Our Valentine’s Market has been rescheduled to Saturday, March 14, due to icy conditions. We’re leaning into the moment and welcoming you to our Belated Valentine Maker’s Market (Defrosted Edition); because you still deserve to treat yourself or your special someone.
  • The Valentine Maker’s Market offers a curated selection of handmade and locally produced goods, making it a destination for thoughtful Valentine’s gifts. Shoppers can browse a wide range of products, including small-batch chocolates, jewelry, leather goods, pottery, clothing, and more, from both indoor and outdoor vendors, all featuring homemade, handmade, or homegrown items crafted with care.
  • Link

***The Playful Parent is a 501(c)(3) dedicated to advocating learning through play and promoting family bonding. This is a FREE resource page, and The Playful Parent is not paid to advertise businesses. If you would like your kid-friendly event added please email me at theplayfulparent@yahoo.com.***

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