Fall Festival Season In Maryland: 20 Events To Check Out

Grab a sweater and make some plans: festivals across Maryland are serving up pumpkin patches, hayrides, and plenty of fall fun from September through November.

Patch has compiled a list of 20 festivals being held across the state. While some events are being held as soon as this weekend, others are running through early November.

Residents looking for more of a scenic drive to catch Maryland's fall foliage this year can do so by sticking to rural roads headed to Sugarloaf Mountain or Catoctin Mountain Park.

A drive out to Harper's Ferry is also worth a weekend trip — bonus points if you're planning on doing the Maryland Heights Trail.

See which fall festivals made Patch's 2026 list below:

Maryland Fall Festivals

• Fall Fun Fest
  5501 Detrick Road, Mt. Airy
  Sept. 4-Nov. 1
• Towson Fall Festival
  Towson Courthouse Gardens, between Pennsylvania and Washington Ave.
  Sept. 5
• Fall Festival at Larriland
  2415 Woodbine Road, Woodbine
  Sept. 8-Oct. 31

• Watersedge Fall Festival 2026
  8278 Bullneck Road, Dundalk
  Sept. 11-13
• 18th Annual Cockeysville Fall Festival
  594 Cranbrook Road, Cockeysville
  Sept. 12
• Fall Festival at Montpelier Farms
  1720 North Crain Highway, Upper Marlboro
  Sept. 12-Nov. 8
• Anne Arundel County Fair
  1450 Generals Hwy, Crownsville
  Sept. 16-20
• Susquehanna Wine & Seafood Fest
  701 Concord St.
  Sept. 19
• 2026 Essex Day Festival
  Eastern Boulevard, between Woodward and Mace
  Sept. 19
• 46th Annual Pumpkin Festival at Butler's Orchard
  22222 Davis Mill Road, Germantown
  Sept. 19-Nov. 1
• Fall Festival at Milburn Orchards
  1495 Appleton Rd, Elkton
  Sept. 19-Nov. 8
• Bowles Farms Corn Maze & Pumpkin Farm
  22880 Budds Creek Road, Clements
  Sept. 25-Oct. 31
• Catonsville Fall Festival
  205 Bloomsbury Ave., Catonsville
  Sept. 26
• Fall Festival at Summers Farm
  7503 Hollow Road, Middletown
  Sept. 26-Nov. 1
• 59th Annual Autumn Glory Festival
  Deep Creek Lake and Garrett County
  Oct. 7-11
• Garden Glow at Ladew
  3535 Jarrettsville Pike, Monkton
  Oct. 14-17
• Oxon Hill Farm Fall Festival
  6411 Oxon Hill Road, Oxon Hill
  Oct. 17
• Hereford Fall Festival
  510 Monkton Road, Monkton
  Oct. 17-18
• Silver Spring Fall-O-Ween
  1 Veterans Place, Silver Spring
  Oct. 25
• Fall Family Festival
  2950 Garrett Road, White Hall
  Nov. 7