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Cockeysville Fall Festival
September 2026 (dates not updated)

Cockeysville Fall Festival

Cranbrook Shopping Center, Cockeysville, MD

Status: Updated 9/15/2025

There will be 1 stage with Regional and Local talent. The entertainment will be Alternative, DJ/Dance/Techno, Electronic, Rock and Top Forty/Pop, and there will be other activities like games, pumpkin patch, beer and wine.
  • # of Exhibitors: 64
  • Juried: no
  • Prize Money: na
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BrickUniverse Annapolis, MD Lego® Fan Expo
September 2026 (dates not updated)

BrickUniverse Annapolis, MD Lego® Fan Expo

Benfield Sportscenter, Millersville, MD

Status: Updated 1/3/2025

  • # of Exhibitors: 15
  • Juried: no
  • Prize Money:
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Annapolis Fall Home Owners Expo
September 2026 (dates not updated)

Annapolis Fall Home Owners Expo

The Byzantium Conference and Event Center, Annapolis, MD

Status: Updated 9/16/2025

There will be 1 stage with National talent. The entertainment will be Variety.
  • # of Exhibitors: tba
  • Juried:
  • Prize Money: na
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Smithsburg Steam Engine and Craft Show
September 2026 (dates not updated)

Smithsburg Steam Engine and Craft Show

Smithsburg Carnival Grounds, Smithsburg, MD

Status: Updated 9/16/2025

  • # of Exhibitors: 145
  • Juried: yes
  • Prize Money: na
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West Annapolis Oktoberfest
September 2026 (dates not updated)

West Annapolis Oktoberfest

Downtown, Annapolis, MD

Status: Updated 8/30/2025

There will be 1 stage with Regional talent. The entertainment will be Ethnic.
  • # of Exhibitors: 110
  • Juried: no
  • Prize Money: na
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Dorchester Center For the Arts Showcase
September 2026 (dates not updated)

Dorchester Center For the Arts Showcase

Historic Downtown High Street, Cambridge, MD

Status: Updated 9/16/2025

  • # of Exhibitors: 125
  • Juried: yes
  • Prize Money: na
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OrangeFest
October 1 - 4, 2026

OrangeFest

Cultural Enrichment Center, Laurel, MD

Status: Updated 11/21/2025

  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
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Frederick's Oktoberfest
October 2 - 3, 2026

Frederick's Oktoberfest

Frederick Fairgrounds, Frederick, MD

Status: Updated 3/10/2026

There will be 3 stages with Regional and Local talent. The entertainment will be Children's, Ethnic and Variety, and there will be other activities like healine bands, dance, children's area, games, contests for adults & kids.
  • # of Exhibitors: 15
  • Juried: no
  • Prize Money: na
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United States Powerboat Show
October 2026 (dates not updated)

United States Powerboat Show

Annapolis City Dock & Harbor, Annapolis, MD

Status: Updated 12/10/2024

  • # of Exhibitors: 400
  • Juried: no
  • Prize Money: na
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Casey Farmers Market - October
October 2026 (dates not updated)

Casey Farmers Market - October

Casey Community Center, Gaithersburg, MD

Status: Updated 4/29/2025

  • # of Exhibitors: 10
  • Juried: yes
  • Prize Money: na
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Easton Fall Craft Fair
October 3, 2026

Easton Fall Craft Fair

Trinity Cathedral Easton -- on grounds, Easton, MD

Status: Updated 2/11/2026

  • # of Exhibitors: 40
  • Juried: no
  • Prize Money: na
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Market of Crafts Galore!
October 3, 2026

Market of Crafts Galore!

Timonium UMC, Timonium, MD

Status: Updated 2/17/2026

  • # of Exhibitors: 50
  • Juried: yes
  • Prize Money: na
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Fall Market
October 3, 2026

Fall Market

Carroll County Agriculture Center, Westminster, MD

Status: Updated 2/4/2026

  • # of Exhibitors: 75
  • Juried: yes
  • Prize Money:
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Monster Market
October 2026 (dates not updated)

Monster Market

Annmarie Sculpture Garden & Arts Center, Dowell, MD

Status: Updated 10/2/2025

  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Fall Marketplace
October 2026 (dates not updated)

Fall Marketplace

Shipley Arena at the Carroll County Ag Center, Westminster, MD

Status: Updated 9/9/2025

  • # of Exhibitors: 100
  • Juried: yes
  • Prize Money:
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Hurlock Fall Festival
October 2026 (dates not updated)

Hurlock Fall Festival

Downtown, Hurlock, MD

Status: Updated 9/30/2025

There will be 1 stage with talent. The entertainment will be Variety, and there will be other activities like parade, train rides.
  • # of Exhibitors: tba
  • Juried:
  • Prize Money: na
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Days End Farm Horse Rescue Benefit Concert
October 2026 (dates not updated)

Days End Farm Horse Rescue Benefit Concert

Days End Farm Horse Rescue, Woodbine, MD

Status: Updated 8/11/2025

There will be 1 stage with Regional and Local talent. The entertainment will be Variety.
  • # of Exhibitors: na
  • Juried: no
  • Prize Money: na
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Darlington Apple Festival
October 2026 (dates not updated)

Darlington Apple Festival

Downtown, Darlington, MD

Status: Updated 3/4/2025

There will be 1 stage with Regional and Local talent. The entertainment will be Bluegrass, Christian, Country, Folk, Gospel, Old-time, Rock and Variety, and there will be other activities like hayride, pony ride, apple pie contest.
  • # of Exhibitors: 312
  • Juried: no
  • Prize Money: na
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Old Bowie Celebrates
October 2026 (dates not updated)

Old Bowie Celebrates

Downtown, Bowie, MD

Status: Updated 9/21/2025

There will be 3 stages with Regional and Local talent. The entertainment will be Beach, Bluegrass, R & B/Soul, Reggae, Rock, Top Forty/Pop and Variety.
  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
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Oakland Mills Fall Festival
October 2026 (dates not updated)

Oakland Mills Fall Festival

Oakland Mills Village Center, Columbia, MD

Status: Updated 9/22/2025

There will be 1 stage with Regional talent. The entertainment will be Children's, Reggae, Rock, Salsa and Variety.
  • # of Exhibitors: 40
  • Juried: no
  • Prize Money: na
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Great Pumpkin Race & Fall Festival
October 2026 (dates not updated)

Great Pumpkin Race & Fall Festival

North Creek Community Center, Montgomery Village, MD

Status: Updated 9/7/2025

There will be 1 stage with Regional talent. The entertainment will be Variety.
  • # of Exhibitors: na
  • Juried: no
  • Prize Money: na
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First Sunday Arts Festival - October
October 4, 2026

First Sunday Arts Festival - October

Downtown Annapolis, Annapolis, MD

Status: Updated 1/8/2026

There will be 3 stages with Local talent. The entertainment will be Variety, and there will be other activities like demonstrations.
  • # of Exhibitors: 130
  • Juried: no
  • Prize Money: na
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Brunswick Railroad Days
October 2026 (dates not updated)

Brunswick Railroad Days

East and West Potomac Street, Brunswick, MD

Status: Updated 6/26/2025

There will be 2 stages with Regional and Local talent. The entertainment will be Bluegrass, Blues, Christian, Country, Folk, Rock, Top Forty/Pop and Variety, and there will be other activities like train rides, train show, amusements.
  • # of Exhibitors: 100
  • Juried: no
  • Prize Money: na
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Main Street Farmers Market - October
October 2026 (dates not updated)

Main Street Farmers Market - October

Main Street Pavilion in the Kentlands, Gaithersburg, MD

Status: Updated 1/16/2025

There will be 1 stage with Local talent. The entertainment will be Americana, Bluegrass, Blues, Classical/Symphony, Country, Ethnic, Folk, Funk, Jazz, Old-time, R & B/Soul, Roots, Variety and World.
  • # of Exhibitors: 30
  • Juried: yes
  • Prize Money: na
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