Travel & outdoor events in Winchester, VA

Search for something you love or check out popular events in your area.

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A Date Night Adventure! - Red Bricks & Blue Views!
Today at 8:00 AM + 39 more
Bloomsbury Square · 100 State Cir
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A Date Night Adventure! - Red Bricks & Blue Views!
Today at 8:00 AM + 39 more
Bloomsbury Square · 100 State Cir
If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!
Tue, Oct 7, 7:00 PM + 3 more
Maryland · The Westin Baltimore Washington Airport - BWI
If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!
Tue, Oct 7, 7:00 PM + 3 more
Maryland · The Westin Baltimore Washington Airport - BWI
Baltimore Tourism Association October 2025 Member Meeting
Thu, Oct 9, 8:30 AM
Linthicum · Maritime Conference Center
Baltimore Tourism Association October 2025 Member Meeting
Thu, Oct 9, 8:30 AM
Linthicum · Maritime Conference Center
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Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled
Bloomsbury Square · Worden Field
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Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled
Bloomsbury Square · Worden Field
Annapolis Murder Mystery: Catch the Killer!
Today at 2:00 PM + 162 more
Bloomsbury Square · 101 State Cir
Annapolis Murder Mystery: Catch the Killer!
Today at 2:00 PM + 162 more
Bloomsbury Square · 101 State Cir
Annapolis epic fun-filled scavenger hunt! - Red Bricks & Blue Views!
Today at 1:00 PM + 90 more
Bloomsbury Square · 100 State Cir
Annapolis epic fun-filled scavenger hunt! - Red Bricks & Blue Views!
Today at 1:00 PM + 90 more
Bloomsbury Square · 100 State Cir
Annapolis Scavenger Hunt: Let’s Roam Red Bricks & Blue Views!
Today at 1:00 PM + 162 more
Bloomsbury Square ·
Annapolis Scavenger Hunt: Let’s Roam Red Bricks & Blue Views!
Today at 1:00 PM + 162 more
Bloomsbury Square ·
Amazing Annapolis Amazing Race & Tour
Today at 2:00 PM + 174 more
Bloomsbury Square · Brown Mustache Coffee, LLC
Amazing Annapolis Amazing Race & Tour
Today at 2:00 PM + 174 more
Bloomsbury Square · Brown Mustache Coffee, LLC
Amazing Annapolis Scavenger Hunt
Today at 2:00 PM + 474 more
Bloomsbury Square · Brown Mustache Coffee, LLC
Amazing Annapolis Scavenger Hunt
Today at 2:00 PM + 474 more
Bloomsbury Square · Brown Mustache Coffee, LLC
Retreat & Revive at Chesapeake Paradise
Sun, Oct 19, 1:00 PM
Deale · Chesapeake Paradise Vacations & Retreats
Retreat & Revive at Chesapeake Paradise
Sun, Oct 19, 1:00 PM
Deale · Chesapeake Paradise Vacations & Retreats
Annapolis Signet Snatch: A Ken Clever Mystery Game
Today at 1:00 PM + 423 more
Bloomsbury Square · 186 Prince George St
Annapolis Signet Snatch: A Ken Clever Mystery Game
Today at 1:00 PM + 423 more
Bloomsbury Square · 186 Prince George St
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Naval Academy Audio Tour: Legends, Landmarks & Legacy in Anne Arundel
Bloomsbury Square · Jeannette Monument
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Naval Academy Audio Tour: Legends, Landmarks & Legacy in Anne Arundel
Bloomsbury Square · Jeannette Monument
Spooky Dinner Cruise on the Bay
Thu, Oct 30, 5:30 PM
Essex · Maryland Party Boat Charters
Spooky Dinner Cruise on the Bay
Thu, Oct 30, 5:30 PM
Essex · Maryland Party Boat Charters
MPB - Middle River Lighted Boat Parade-Family Friendly
Sat, Nov 29, 4:00 PM
Essex · Maryland Party Boat Charters
MPB - Middle River Lighted Boat Parade-Family Friendly
Sat, Nov 29, 4:00 PM
Essex · Maryland Party Boat Charters
World Is Your Oyster Fest 2025!
Thu, Oct 2, 5:30 PM
Washington Village/Pigtown · B&O Railroad Museum
World Is Your Oyster Fest 2025!
Thu, Oct 2, 5:30 PM
Washington Village/Pigtown · B&O Railroad Museum
The ISI Life™ Ski/Snowboard Day Trip!
Wed, Jan 28, 9:00 AM
Seven Springs · Seven Springs Mountain Resort
The ISI Life™ Ski/Snowboard Day Trip!
Wed, Jan 28, 9:00 AM
Seven Springs · Seven Springs Mountain Resort
Leave No Trace Hike with 52 Hike Challenge at Staple Bend Tunnel
Sat, Oct 11, 10:00 AM
Pennsylvania · Staple Bend Tunnel Trail
Leave No Trace Hike with 52 Hike Challenge at Staple Bend Tunnel
Sat, Oct 11, 10:00 AM
Pennsylvania · Staple Bend Tunnel Trail
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Pansy Tour
Thursday at 11:00 AM
Rosegarden · Ashcombe Farm and Greenhouses
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Pansy Tour
Thursday at 11:00 AM
Rosegarden · Ashcombe Farm and Greenhouses
Kayaking 1PM
Today at 1:00 PM
Holliday · Starry Parking Lot
Kayaking 1PM
Today at 1:00 PM
Holliday · Starry Parking Lot
If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!
Tue, Oct 14, 7:30 PM + 4 more
Overlea · Hilton Garden Inn Baltimore/White Marsh
If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!
Tue, Oct 14, 7:30 PM + 4 more
Overlea · Hilton Garden Inn Baltimore/White Marsh

Trends in Winchester

Explore more trends

Frequently asked questions about Winchester

What are the best events to attend?

According to Eventbrite, the best events are:

If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!

Baltimore Tourism Association October 2025 Member Meeting

Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled

Annapolis Murder Mystery: Catch the Killer!

Which events are currently trending in Winchester?

The trending searches this month in Winchester are:

labor day weekend

events happening today near me

fall

rodeo

Which events are coming up?

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

A Date Night Adventure! - Red Bricks & Blue Views!

Annapolis epic fun-filled scavenger hunt! - Red Bricks & Blue Views!

Annapolis Scavenger Hunt: Let’s Roam Red Bricks & Blue Views!

Annapolis Signet Snatch: A Ken Clever Mystery Game

A Date Night Adventure! - Red Bricks & Blue Views!

A Date Night Adventure! - Red Bricks & Blue Views!

If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!

If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!

Baltimore Tourism Association October 2025 Member Meeting

Baltimore Tourism Association October 2025 Member Meeting

Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled

Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled

Annapolis Murder Mystery: Catch the Killer!

Annapolis Murder Mystery: Catch the Killer!

Annapolis epic fun-filled scavenger hunt! - Red Bricks & Blue Views!

Annapolis epic fun-filled scavenger hunt! - Red Bricks & Blue Views!

Annapolis Scavenger Hunt: Let’s Roam Red Bricks & Blue Views!

Annapolis Scavenger Hunt: Let’s Roam Red Bricks & Blue Views!

Amazing Annapolis Amazing Race & Tour

Amazing Annapolis Amazing Race & Tour

Amazing Annapolis Scavenger Hunt

Amazing Annapolis Scavenger Hunt

Retreat & Revive at Chesapeake Paradise

Retreat & Revive at Chesapeake Paradise

Annapolis Signet Snatch: A Ken Clever Mystery Game

Annapolis Signet Snatch: A Ken Clever Mystery Game

Naval Academy Audio Tour: Legends, Landmarks & Legacy in Anne Arundel

Naval Academy Audio Tour: Legends, Landmarks & Legacy in Anne Arundel

Spooky Dinner Cruise on the Bay

Spooky Dinner Cruise on the Bay

MPB - Middle River Lighted Boat Parade-Family Friendly

MPB - Middle River Lighted Boat Parade-Family Friendly

World Is Your Oyster Fest 2025!

World Is Your Oyster Fest 2025!

The ISI Life™ Ski/Snowboard Day Trip!

The ISI Life™ Ski/Snowboard Day Trip!

Leave No Trace Hike with 52 Hike Challenge at Staple Bend Tunnel

Leave No Trace Hike with 52 Hike Challenge at Staple Bend Tunnel

Pansy Tour

Pansy Tour

Kayaking 1PM

Kayaking 1PM

If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!

If you Travel & Live Luxe in Baltimore, MD, You Need to Own a Travel Biz!

Things to do around Winchester

Trends in Winchester

1. Labor day weekend

2. Events happening today near me

3. Fall

4. Rodeo

5. Craft fairs

6. Car show

7. Drag

8. Halloween

9. Live concerts

10. October

11. Kids events

12. Sip and paint