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Events and Things to do in Middletown, MD

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Fall Back Hallo-Wine Fest 2026
Sat, Oct 31, 1:00 PM
Maryland · Washington County Agricultural Education Center
Fall Back Hallo-Wine Fest 2026
Sat, Oct 31, 1:00 PM
Maryland · Washington County Agricultural Education Center
Going fast
Emo Night!
Saturday at 6:00 PM
Rosedale · Olde Mother Brewing
Going fast
Emo Night!
Saturday at 6:00 PM
Rosedale · Olde Mother Brewing
Frederick Vntg Fest October 17-18
Sat, Oct 17, 11:00 AM
Mount Olivet Heights · Frederick Fairgrounds - Home of The Great Frederick Fair
Frederick Vntg Fest October 17-18
Sat, Oct 17, 11:00 AM
Mount Olivet Heights · Frederick Fairgrounds - Home of The Great Frederick Fair
Cris Jacobs + Pressing Strings
Thu, Oct 15, 7:00 PM
Mount Olivet Heights · RAK Brewing Co
Cris Jacobs + Pressing Strings
Thu, Oct 15, 7:00 PM
Mount Olivet Heights · RAK Brewing Co
Almost full
Annual Frederick Health Auxiliary Fashion Show
Wed, Oct 28, 5:00 PM
Overlook · Dutch's Daughter
Almost full
Annual Frederick Health Auxiliary Fashion Show
Wed, Oct 28, 5:00 PM
Overlook · Dutch's Daughter
Almost full
5th Annual Mary Ann Martin Black Cat Cash Bingo
Sunday at 12:00 PM
Willowcrest · Frederick Elks 684
Almost full
5th Annual Mary Ann Martin Black Cat Cash Bingo
Sunday at 12:00 PM
Willowcrest · Frederick Elks 684
Sales end soon
Autumn Reggae Wine & Music Festival 2026 | Linganore Winecellars
Saturday at 10:00 AM + 1 more
Maryland · Linganore Winecellars
Sales end soon
Autumn Reggae Wine & Music Festival 2026 | Linganore Winecellars
Saturday at 10:00 AM + 1 more
Maryland · Linganore Winecellars
Appalachian Oddities Faire — Saturday Oddities Market
Sat, Oct 17, 11:00 AM
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Appalachian Oddities Faire — Saturday Oddities Market
Sat, Oct 17, 11:00 AM
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Quad State Holiday Pickle Fest on National Pickle Day
Sat, Nov 14, 11:00 AM
Maryland · Washington County Agricultural Education Center
Quad State Holiday Pickle Fest on National Pickle Day
Sat, Nov 14, 11:00 AM
Maryland · Washington County Agricultural Education Center
Halloween After Dark
Sat, Oct 31, 9:00 PM
Mount Olivet Heights · Mountain City Lodge
Halloween After Dark
Sat, Oct 31, 9:00 PM
Mount Olivet Heights · Mountain City Lodge
Sales end soon
Candle Making Workshop
Thursday at 5:30 PM + 15 more
Spring Valley · LiveYoung Candle Co
Sales end soon
Candle Making Workshop
Thursday at 5:30 PM + 15 more
Spring Valley · LiveYoung Candle Co
Almost full
Dark Phoenix After Dark — Oddities Ball Performance Add-On
Sat, Oct 17, 9:30 PM + 1 more
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Almost full
Dark Phoenix After Dark — Oddities Ball Performance Add-On
Sat, Oct 17, 9:30 PM + 1 more
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Almost full
The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment
Sat, Oct 17, 8:00 PM
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Almost full
The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment
Sat, Oct 17, 8:00 PM
West Virginia · Clarion Inn Harpers Ferry-Charles Town
Foodies + New Friends: Frederick | Dinner with Strangers
Fri, Nov 6, 7:00 PM + 1 more
Mount Olivet Heights · Restaurant of the Week
Foodies + New Friends: Frederick | Dinner with Strangers
Fri, Nov 6, 7:00 PM + 1 more
Mount Olivet Heights · Restaurant of the Week
Sales end soon
Crush Your TBR
Tomorrow at 6:00 PM
Mount Olivet Heights · The Banyan
Sales end soon
Crush Your TBR
Tomorrow at 6:00 PM
Mount Olivet Heights · The Banyan
America 250 with the Frederick Catoctones
Sat, Oct 24, 3:00 PM
Rosedale · Frederick Church of the Brethren
America 250 with the Frederick Catoctones
Sat, Oct 24, 3:00 PM
Rosedale · Frederick Church of the Brethren
DRAG ME TO HALLOWEEN: A Costume Party Like No Other @ Steinhardt Brewery
Fri, Oct 23, 7:30 PM
Mount Olivet Heights · Steinhardt Brewing Company
DRAG ME TO HALLOWEEN: A Costume Party Like No Other @ Steinhardt Brewery
Fri, Oct 23, 7:30 PM
Mount Olivet Heights · Steinhardt Brewing Company
Almost full
ACOTAR Midnight release at Periwinkle & Prose
Mon, Oct 26, 9:00 PM
Mount Olivet Heights · 106 N Market St
Almost full
ACOTAR Midnight release at Periwinkle & Prose
Mon, Oct 26, 9:00 PM
Mount Olivet Heights · 106 N Market St
Hot Brass & Cool Grooves featuring Scott Ambush
Sat, Oct 17, 7:30 PM
Brigadoon · Frederick High School
Hot Brass & Cool Grooves featuring Scott Ambush
Sat, Oct 17, 7:30 PM
Brigadoon · Frederick High School
Several Species: The PINK FLOYD Experience - Night 1: Dark Side of The Moon
Fri, Nov 13, 8:00 PM
Frederick Manor · Live At Hub City Vinyl
Several Species: The PINK FLOYD Experience - Night 1: Dark Side of The Moon
Fri, Nov 13, 8:00 PM
Frederick Manor · Live At Hub City Vinyl

Trends in Middletown

Explore more trends

Explore more trends

Frequently asked questions about Middletown

What are the best events to attend?

According to Eventbrite, the best events are:

Fall Back Hallo-Wine Fest 2026

Frederick Vntg Fest October 17-18

Cris Jacobs + Pressing Strings

Annual Frederick Health Auxiliary Fashion Show

Which events are currently trending in Middletown?

The trending searches this month in Middletown are:

quad pickle fest

mckinnon studio

“silent auction”

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Candle Making Workshop

Autumn Reggae Wine & Music Festival 2026 | Linganore Winecellars