Hi Adventure Fam!
Happy New month! It's finally October and Maryland clearly got the memo!
This weekend is packed with festivals, food, cultural events, county fair fun and plenty of activities for the kids. And if you're looking specifically for pumpkin patches and fall farms, don't worry, I've got those covered too!
This Weekend’s Top Picks
- Fell’s Point Fun Festival
One of Baltimore’s biggest neighborhood celebrations is back, and this year marks its 60th anniversary!
Six blocks of historic Fell’s Point will be filled with live music, food, local vendors, artisans and entertainment, all with the waterfront as the backdrop.
Cost: FREE admission
Best for: Families who want food + music + a fun city outing
Deyewa Tip: Make a day of it and spend some time walking the waterfront while you're there.
2. Panafest: Taste of Africa
Celebrate African culture through food, music, dance, fashion, art and more at this weekend’s Panafest Taste of Africa.
Expect cultural experiences representing countries across the continent, plenty of food and a dedicated area for kids.
Cost: FREE admission with RSVP
Best for: Families looking for food + culture + entertainment
3. Calvert County Fair
September 30–October 4 | Prince Frederick
County fair season isn't quite over yet!
The Calvert County Fair wraps up this weekend with animals, agricultural exhibits, competitions, entertainment, food and all the classic fair fun.
Best for: All ages
Good to know: Sunday is the final day of the 2026 fair.
Deyewa Tested
Magnolia Meadow Farms
We visit Magnolia Meadow Farms every year for their fall season, and this one definitely deserves a spot on your Maryland fall list!
There are 20+ activities for the kids, including Maryland’s largest corn maze, mini ziplines, a jumping pillow, mountain slides, pedal carts, farm animals, hayrides and plenty more.
You can also pick pumpkins and flowers while you're there, although those and a few other activities are additional costs.
Deyewa Tip: Give yourself a few hours here. The farm is spread out and there is plenty for the kids to explore. I would say at least 3 hours.
📍 Thurmont, MD
Free Family Find
College Park Day
October 3 | 12–6 PM | College Park
This might be one of the BEST free family events happening this weekend.
College Park Day takes over the College Park Aviation Museum and Airport with three stages of entertainment, inflatables, carnival-style games, wandering performers, arts and crafts vendors and a helicopter fly-in.
Admission to the College Park Aviation Museum is FREE during the event!
Cost: FREE
Best for: All ages, especially airplane-loving kids
Worth the Drive?
Easton’s Fall Kickoff
October 2–3 | Easton
If you're up for a drive to the Eastern Shore, downtown Easton is kicking off October with an entire weekend of activities.
Walk the giant pumpkin trail, catch live music and outdoor entertainment, and explore downtown shops and restaurants.
Saturday brings even more for families, including free kids' fall activities, pumpkin decorating, glassblowing demonstrations and a fall craft fair.
Cost: Many activities are FREE
📍 Easton, Talbot County
This would also be a fun excuse to spend the day exploring downtown Easton instead of driving down for just one event
Plan Ahead
Carroll County Farm Museum Traditional Arts Festival
October 10 | Westminster
Looking ahead to next weekend, the Carroll County Farm Museum is hosting its Traditional Arts Festival.
Expect live music, food trucks, craft vendors and fall activities plus a free pumpkin for the first 500 kids.
📍 Carroll County Farm Museum | Westminster
Put this one on next weekend's calendar now!
More Happening Around Maryland This Weekend
🍛 Flavors by Adunni Pop-Up Experience
Oct. 2 | Laurel
Authentic Nigerian favorites and Afro-fusion dishes from 6–8 PM, including Asun Jollof Rice, Suya Pasta, Puff Puff Flights and street food. Preordering is strongly recommended.
🍎 Darlington Apple Festival
Oct. 3 | Darlington
A free one-day Harford County tradition with crafts, food, entertainment, art, a country market and plenty of apple-themed fun.
🍽️ Taste of Bethesda
Oct. 3 | Bethesda
Free admission with food available for purchase, plus four stages of entertainment and activities for kids.
🌾 Montgomery Parks Harvest Festival
Oct. 3 | Derwood
Hayrides, farm animals, crafts, demonstrations, entertainment and hands-on family activities.
🐴 Old Maryland Farm Fall Farm Festival
Oct. 3 | Upper Marlboro
A FREE family event with a pumpkin patch, farm animals, pumpkin bowling, hobby-horse racing, games and hands-on activities.
🤠 Redeye Rodeo
Oct. 3 | Gaithersburg
Bull riding, barrel racing, a mechanical bull, food and vendors at the Montgomery County Fairgrounds.
🎨 Frederick Hispanic Heritage Festival
Oct. 3 | Frederick
Celebrate Hispanic heritage with live music, dancing, traditional costumes, food and kids' activities.
🚂 Hurlock Fall Festival & Train Rides
Oct. 3 | Hurlock
A FREE Eastern Shore festival with train rides, a Main Street parade, arts and crafts, music and food.
🎶 Mount Airy Oktoberfest
Oct. 3 | Mount Airy
Spend Saturday enjoying food, live music and Oktoberfest-inspired festivities.
🚂 Brunswick Railroad Days
Oct. 3–4 | Brunswick
A FREE weekend celebrating Brunswick's railroad heritage with model trains, live music, artisans, food and kids' activities.
🌾 Fall Fest at Rose Hill Manor
Oct. 3–4 | Frederick
A FREE family weekend with agricultural demonstrations, hayrides, crafts, food and hands-on activities.
🍂 Looking for a Fall Farm Instead?
There are plenty open this weekend too!
🌻 Magnolia Meadow Farms — Thurmont
🌽 Gaver Farm — Mount Airy
🎃 Summers Farm — Middletown
🎃 Butler’s Orchard — Germantown
🌽 MD Corn Maze — Gambrills
🌽 Montpelier Farms — Upper Marlboro
🎃 Knightongale Farm — Harwood
🍎 Larriland Farm — Woodbine
🐐 Clark’s Elioak Farm — Ellicott City
🍂 Greenstreet Gardens — Lothian
🎃 Jumbo’s Pumpkin Patch — Middletown
🍎 Milburn Orchards — Elkton
Coming Up on Deyewa
Next week because its still fall festival season I’m going to continue working on:
Maryland fall farms and festivals
If there’s somewhere you think I should include, hit reply and tell me!
I actually read the responses, and they help me decide what to cover next.
Before I head out though, I want to leave you will a prayer as you wrap up the week
I pray that whatever you lay your hands on will prosper and that God will meet you at the point of your needs. If there is something you are crying out to God for, I pray this is your season to get a testimony. May God show you how wide and how deep his love is for you. Amen
See you next weekend,
Lola Deyewa
Helping Maryland families find fun, low-stress adventures worth the time, money, and drive.
Instagram: @thedeyewa Website: Deyewa.com
