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Cultural Enrichment, Music, and Arts Festival
August 26 - 29, 2026

Cultural Enrichment, Music, and Arts Festival

Cultural Enrichment Center, Laurel, MD

Status: Updated 2/27/2026

  • # of Exhibitors: 80
  • Juried: no
  • Prize Money:
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Ocean City Jeep Week
August 27 - 30, 2026

Ocean City Jeep Week

Various Locations, Ocean City, MD

Status: Updated 8/10/2026

  • # of Exhibitors: 100
  • Juried: no
  • Prize Money: na
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Maryland State Fair
August 27 - September 13, 2026

Maryland State Fair

State Fairgrounds, Timonium, MD

Status: Updated 8/10/2026

There will be 1 stage with National and Regional talent. The entertainment will be Country, Rock and Variety.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Fourth Friday Street Festival - August
August 28, 2026

Fourth Friday Street Festival - August

Downtown, Pocomoke City, MD

Status: Updated 8/9/2026

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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Maryland Renaissance Festival
August 29 - October 25, 2026

Maryland Renaissance Festival

Crownsville Road, Annapolis, MD

Status: Updated 4/14/2026

There will be 10 stages with International, National and Regional talent. The entertainment will be Folk and Variety, and there will be other activities like children's area, games.
  • # of Exhibitors: 118
  • Juried: yes
  • Prize Money: na
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National Hard Crab Derby
September 3 - 6, 2026

National Hard Crab Derby

Somer's Cove Marina, Crisfield, MD

Status: Updated 6/23/2026

There will be 1 stage with Regional and Local talent. The entertainment will be , and there will be other activities like crab races, crab picking contest, boat docking contest.
  • # of Exhibitors: 30
  • Juried: no
  • Prize Money: na
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Casey Farmers Market - September
September 3 - 24, 2026

Casey Farmers Market - September

Casey Community Center, Gaithersburg, MD

Status: Updated 6/10/2026

  • # of Exhibitors: 10
  • Juried: yes
  • Prize Money: na
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Western Maryland Street Rod Round-Up
September 4 - 6, 2026

Western Maryland Street Rod Round-Up

Allegany County Fairgrounds, Cumberland, MD

Status: Updated 7/26/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Old-time, Rock, Top Forty/Pop and Variety.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Greenbelt Labor Day Festival
September 4 - 7, 2026

Greenbelt Labor Day Festival

Roosevelt Center, Greenbelt, MD

Status: Updated 6/24/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Variety, and there will be other activities like parade, carnival rides, kids' games, local art contest.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Market of Crafts Galore! - September
September 5, 2026

Market of Crafts Galore! - September

Grace Lutheran Church of Lutherville, Lutherville-Timonium, MD

Status: Updated 8/17/2026

  • # of Exhibitors: 50
  • Juried: yes
  • Prize Money: na
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Stumble Into Fall
September 5 - 6, 2026

Stumble Into Fall

Barrel Bodega, Hagerstown, MD

Status: Updated 7/9/2026

  • # of Exhibitors: 23
  • Juried: yes
  • Prize Money:
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Main Street Farmers Market - September
September 5 - 26, 2026

Main Street Farmers Market - September

Main Street Pavilion in the Kentlands, Gaithersburg, MD

Status: Updated 8/10/2026

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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Fall Outdoor Flea Market
September 2026 (dates not updated)

Fall Outdoor Flea Market

North Creek Community Center, Montgomery Village, MD

Status: Updated 7/26/2025

  • # of Exhibitors: 68
  • Juried: no
  • Prize Money: na
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First Sunday Arts Festival - September
September 6, 2026

First Sunday Arts Festival - September

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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Deal Island Skipjack Races and Festival
September 6 - 7, 2026

Deal Island Skipjack Races and Festival

Deal Island Harbor, Deal Island, MD

Status: Updated 8/13/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Christian, Country, DJ/Dance/Techno, Gospel, Rock and Top Forty/Pop.
  • # of Exhibitors: 30
  • Juried: no
  • Prize Money: na
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Baltimore Farmer's Market - September
September 6 - 27, 2026

Baltimore Farmer's Market - September

Holiday and Saratoga Streets, Baltimore, MD

Status: Updated 3/30/2026

  • # of Exhibitors: tba
  • Juried: yes
  • Prize Money: na
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Gaithersburg Labor Day Parade
September 7, 2026

Gaithersburg Labor Day Parade

Olde Towne Gaithersburg, Gaithersburg, MD

Status: Updated 8/10/2026

  • # of Exhibitors: na
  • Juried: no
  • Prize Money: na
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Labor Day Parade and Festival
September 7, 2026

Labor Day Parade and Festival

Downtown, Kensington, MD

Status: Updated 8/13/2026

  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Ocean City Motorcycle SwapMeet
September 10 - 13, 2026

Ocean City Motorcycle SwapMeet

Strawberry Crossroads, Pittsfield, MD

Status: Updated 8/21/2026

  • # of Exhibitors: Tbd
  • Juried: no
  • Prize Money: na
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Fall Home Lifestyles Expo
September 11 - 13, 2026

Fall Home Lifestyles Expo

3901 Calverton Blvd, Calverton, MD

Status: Updated 3/9/2026

There will be 1 stage with Local talent. The entertainment will be DJ/Dance/Techno, Gospel, Jazz and Reggae, and there will be other activities like stage presentations.
  • # of Exhibitors: 20
  • Juried: no
  • Prize Money: na
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Harford Plein Air Festival
September 11 - 13, 2026

Harford Plein Air Festival

Bel Air Armory, Bel Air, MD

Status: Updated 4/20/2026

  • # of Exhibitors: 30
  • Juried: yes
  • Prize Money: $100-$3,000
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Locust Point Festival
September 12, 2026

Locust Point Festival

Latrobe Park, Baltimore, MD

Status: Updated 8/24/2026

There will be 1 stage with Local talent. The entertainment will be Variety.
  • # of Exhibitors: 20
  • Juried: no
  • Prize Money: na
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Cockeysville Fall Festival
September 12, 2026

Cockeysville Fall Festival

Cranbrook Shopping Center, Cockeysville, MD

Status: Updated 8/23/2026

There will be 1 stage with Regional and Local talent. The entertainment will be Alternative, DJ/Dance/Techno, Electronic, Rock and Top Forty/Pop.
  • # of Exhibitors: 64
  • Juried: no
  • Prize Money: na
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Frederick's in the Street
September 12, 2026

Frederick's in the Street

Market Street, Frederick, MD

Status: Updated 4/30/2026

There will be 5 stages with National, Regional and Local talent. The entertainment will be Alternative, Bluegrass, Blues, Country, Funk, R & B/Soul, Reggae, Rock, Roots and Swing, and there will be other activities like parade, kids' block, mile run.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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