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Search filters: Events in Maryland.

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Butler's Orchard Pumpkin Festival
September - November 2026 (dates not updated)

Butler's Orchard Pumpkin Festival

Butler's Orchard, Germantown, MD

Status: Updated 8/19/2025

There will be 1 stage with Regional and Local talent. The entertainment will be Bluegrass, Country and Variety, and there will be other activities like pumpkins, hayrides, giant slides, pony rides, hayloft jumping, straw maze.
  • # of Exhibitors: na
  • Juried: no
  • Prize Money:
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Westminster Fallfest
September 24 - 27, 2026

Westminster Fallfest

City Park, Westminster, MD

Status: Updated 7/28/2026

There will be 2 stages with Regional and Local talent. The entertainment will be Alternative, Beach, Bluegrass, Cajun/Zydeco, Country, Funk, Old-time, R & B/Soul, Reggae, Rock and Top Forty/Pop, and there will be other activities like beer/wine garden, craft/vendors, games, kids' court, live music, carnival rides.
  • # of Exhibitors: 80+
  • Juried: yes
  • Prize Money: na
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Calvert County Fair
September 2026 (dates not updated)

Calvert County Fair

Calvert County Fairgrounds, Prince Frederick, MD

Status: Updated 9/8/2025

  • # of Exhibitors: tba
  • Juried:
  • Prize Money: na
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Elkton Fall Fest
September 25 - 26, 2026

Elkton Fall Fest

Downtown, Elkton, MD

Status: Updated 1/13/2026

There will be 2 stages with Regional and Local talent. The entertainment will be Bluegrass, Cajun/Zydeco, Children's, Country, DJ/Dance/Techno, R & B/Soul, Rock, Top Forty/Pop and Variety, and there will be other activities like children's games, inflatables, climbing wall.
  • # of Exhibitors: 175
  • Juried: no
  • Prize Money: na
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Saint Theodore Greek Cultural Festival
September 25 - 27, 2026

Saint Theodore Greek Cultural Festival

St. Theodore Greek Orthodox Church, Lanham, MD

Status: Updated 7/19/2026

There will be 1 stage with Regional talent. The entertainment will be World, and there will be other activities like face painting, games, etc.
  • # of Exhibitors: 6
  • Juried: no
  • Prize Money: na
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Fourth Friday Street Festival - September
September 2026 (dates not updated)

Fourth Friday Street Festival - September

Downtown, Pocomoke City, MD

Status: Updated 3/11/2025

There will be 1 stage with Local talent. The entertainment will be Classical/Symphony and Jazz.
  • # of Exhibitors: 11
  • Juried: no
  • Prize Money: na
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Taneytown Harvest Festival
September 26, 2026

Taneytown Harvest Festival

Taneytown Memorial Park, Taneytown, MD

Status: Updated 1/13/2026

There will be 1 stage with National talent. The entertainment will be Rock and Rockabilly.
  • # of Exhibitors: 40
  • Juried: no
  • Prize Money: na
2.57/5
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Pigtown Festival
September 26, 2026

Pigtown Festival

Pigtown Main ST, Baltimore, MD

Status: Updated 8/16/2026

There will be 1 stage with Local talent. The entertainment will be Variety.
  • # of Exhibitors: 60
  • Juried: no
  • Prize Money: na
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Harford County Wine Festival
September 26, 2026

Harford County Wine Festival

Rockfield Manor, Bel Air, MD

Status: Updated 8/20/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Blues, Children's, Country, Rock, Top Forty/Pop and Variety.
  • # of Exhibitors: Tbd
  • Juried: no
  • Prize Money: na
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Middletown Heritage Festival
September 26, 2026

Middletown Heritage Festival

Downtown, Middletown, MD

Status: Updated 8/22/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Bluegrass, Country, Folk, Old-time, Rock and Variety.
  • # of Exhibitors: 70
  • Juried: no
  • Prize Money: na
2.71/5
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Mount Airy Lions Club Fall Yard Sale / Flea Market
September 26, 2026

Mount Airy Lions Club Fall Yard Sale / Flea Market

MAVFC Carnival Grounds, Mount Airy, MD

Status: Updated 8/23/2026

  • # of Exhibitors: 350
  • Juried: no
  • Prize Money: na
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Catonsville Fall Festival
September 26, 2026

Catonsville Fall Festival

The Children's Home, Catonsville, MD

Status: Updated 7/28/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Alternative, Americana, Beach, Bluegrass, Blues, Cajun/Zydeco, Country, DJ/Dance/Techno, Folk, Jazz, Reggae, Rock and Swing, and there will be other activities like kid zone.
  • # of Exhibitors: 120
  • Juried: yes
  • Prize Money: Ribbons
2.79/5
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Washington Grove Fall Arts & Crafts Festival
September 26, 2026

Washington Grove Fall Arts & Crafts Festival

Outdoors, Washington Grove, MD

Status: Updated 8/11/2026

  • # of Exhibitors: 25
  • Juried: no
  • Prize Money:
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Health, Hope & Harmony Festival
September 26, 2026

Health, Hope & Harmony Festival

Hoen Lithograph Building, Baltimore, MD

Status: Updated 8/14/2026

There will be 1 stage with Local talent. The entertainment will be DJ/Dance/Techno and Face Painting, and there will be other activities like rock painting, produce/food giveway, raffles.
  • # of Exhibitors: 40
  • Juried: no
  • Prize Money:
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International Gem and Jewelry Show - Timonium
September 2026 (dates not updated)

International Gem and Jewelry Show - Timonium

Maryland State Fairgrounds, Timonium, MD

Status: Updated 9/9/2025

  • # of Exhibitors: tba
  • Juried: yes
  • Prize Money: na
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West Annapolis Oktoberfest
September 27, 2026

West Annapolis Oktoberfest

Downtown, Annapolis, MD

Status: Updated 8/16/2026

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 27, 2026

Dorchester Center For the Arts Showcase

Historic Downtown High Street, Cambridge, MD

Status: Updated 8/16/2026

  • # of Exhibitors: 125
  • Juried: yes
  • 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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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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Casey Farmers Market - October
October 1 - 29, 2026

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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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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Fell's Point Fun Festival
October 2 - 4, 2026

Fell's Point Fun Festival

Historic Waterfront at Fell's Point, Baltimore, MD

Web: fellspointfest.com

Status: Updated 5/1/2026

There will be 2 stages with National, Regional and Local talent. The entertainment will be Blues, Cajun/Zydeco, Country, Folk, Jazz, R & B/Soul, Reggae, Rock, Swing, Top Forty/Pop and Variety, and there will be other activities like street performers, childrens area, beer gardens.
  • # of Exhibitors: 200
  • Juried: yes
  • Prize Money: na
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