Amazing Race near Winchester, Maryland

Are you a fan of the Amazing Race? Grab some teammates and dash around the city while deciphering questions and searching for answers. You will need to be the quickest and the smartest to win top spot on our Puzzling Adventures leaderboard!

Embark on a thrilling adventure in Annapolis! Unravel the city's rich history, from its days as the US capital to its vibrant present. Discover the tales of Princess Anne, Abraham Lincoln, and Duke Ellington. Marvel at the city's architectural wonders, learn about the oldest living people in Maryland, and even snap a selfie with your favorite statue. Uncover secrets of the past and solve riddles that will challenge your mind. This is Annapolis like you've never seen it before!

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About Puzzling Adventures

Looking for things to do with your date, friends, kids, teenagers, or other family?

Puzzling Adventures are a cross between a scavenger hunt, an amazing race, and a self-guided walking tour. Enjoy this unique outdoor activity and experience sightseeing in a fun new way. Each city route consists of a series of locations that you are guided to where you answer questions or solve puzzles to receive your next instruction. All you need is your own mobile device with a data connection.

Enjoyed by people of all ages...

From children to seniors, from groups to individuals, our adventures cater to all ages and preferences. Nearly all our experiences are meticulously designed and accommodate wheelchairs and strollers, ensuring inclusivity for all. Each adventure is thoughtfully curated to blend entertainment and education, with something to captivate every participant.

Explore at your leisure, on your terms...

Because our adventures are self-guided you can play any time on any day - no reservations required. Complete the adventure as quickly as possible to win first place or take your time to enjoy the sights, sounds, smells and tastes of the various locations you will visit.

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Puzzling Adventures near Winchester

What are people saying about Puzzling Adventures?

Customer Reviews

This scavenger hunt was great for the whole family. We had ages 3 to 63 on our team and we all had a wonderful time!

Karen B.

This was really fun, it was a nice day and we learned a lot!

Bill S.

This was so much fun! What a great adventure!

Michele P.

Image © The Fabulous Four

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Puzzling Adventures Highlights

Outdoor activity
250+ Locations
No reservations
Accessible
Enriching
Informative
Team building
Flat rate price
Kid friendly
Exploration
Photo Challenges

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Some studies have shown that natural outdoor environments in urban spaces are more enticing for physical activity and are more likely to motivate people to exercise, leading to higher levels of fitness. Whether it is a park in your neighborhood or exploring the vast landscapes of national forests and grasslands, there are benefits to be had when we step outside.

United States Department of Agriculture

https://www.fs.usda.gov/features/wellness-benefits-great-outdoors

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Rendering Map

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View Purchase Options

directions

25 Northwest St., Annapolis, MD 21401

More Information

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Directory

Walking Tour

Lands End Walking Tour Georgetown East Walking Tour Victor Haven Walking Tour Captains Choice Walking Tour Providence Historical Walking Tour Westwinds Walking Tour Ferry Farms Walking Tour Severnside Walking Tour Annapolis Roads Walking Tour Heritage Walking Tour Greenbriar Walking Tour Mariners Point Walking Tour Tyler Heights Walking Tour Forest Meadows Walking Tour Round View Walking Tour Cedarwood Cove Walking Tour Weems Creek Walking Tour Browns Woods Villa Walking Tour Pendennis Mount Walking Tour Pines On Severn Walking Tour Mariners Cove Walking Tour Severn Forest Walking Tour Bloomsbury Square Walking Tour Providence Cove Walking Tour Admiral Heights Walking Tour Martins Cove Farm Walking Tour The Village Walking Tour Old Annapolis Neck Walking Tour The Ridings Walking Tour Bancroft Walking Tour Truxton Heights Walking Tour West Annapolis Walking Tour Manresa Walking Tour Eastport Walking Tour Beechwood On The Burley Walking Tour Loretta Heights Walking Tour Colony Hills Walking Tour Robinwood Walking Tour Dulls Corner Walking Tour Eatons Landing Walking Tour Hillsmere Shores Walking Tour Harkness Creek Park Walking Tour New Point Walking Tour Riverview Manor Walking Tour Greenbriar Gardens Walking Tour Captains Walk Walking Tour Annapolis Walking Tour Primrose Acres Walking Tour Lindamoor On The Severn Walking Tour Naval Academy Walking Tour Bywater Estates Walking Tour Brice Manor Walking Tour Threemile Oak Corner Walking Tour Market Quay Walking Tour Annapolis Overlook Walking Tour Keys Farm Walking Tour Baytowne Village Walking Tour West Woods Walking Tour Colonial Manor Estates Walking Tour Parole Walking Tour Wardour Bluffs Walking Tour Lincoln Heights Walking Tour Bay Ridge Junction Walking Tour Elktonia Walking Tour Homewood Walking Tour Severn Grove Walking Tour Knightsbridge Walking Tour Bestgate Terrace Walking Tour Hidden Point Walking Tour Forest Villa Walking Tour Wilshire Walking Tour Romar Estates Walking Tour Town Home Village Walking Tour Harness Woods Walking Tour Dreams Landing Walking Tour Painters Hill Walking Tour Wetheridge Estates Walking Tour Dorsey Heights Walking Tour The Courtyards Walking Tour Great Meadows Walking Tour Winchester Walking Tour Hunt Meadows Walking Tour Watergate Village Walking Tour Indian Hills Walking Tour Gentry Walking Tour Luce Creek Walking Tour Timber Creek Walking Tour Bay View Heights Walking Tour Wilelinor Estates Walking Tour Anchorage Walking Tour Browns Woods Walking Tour The Meadows Walking Tour Dellwood Walking Tour Bembe Beach Walking Tour Wardour Walking Tour Rundelac Farm Walking Tour Hickory Hills Walking Tour Sturbridge Walking Tour Winchester On The Severn Walking Tour Eastport Terrace Walking Tour

Treasure Hunt

Providence Historical Treasure Hunt Luce Creek Treasure Hunt Brice Manor Treasure Hunt Pendennis Mount Treasure Hunt Lands End Treasure Hunt Colonial Manor Estates Treasure Hunt Bestgate Terrace Treasure Hunt Gentry Treasure Hunt The Meadows Treasure Hunt Town Home Village Treasure Hunt Manresa Treasure Hunt Dorsey Heights Treasure Hunt Old Annapolis Neck Treasure Hunt Cedarwood Cove Treasure Hunt Sturbridge Treasure Hunt Bembe Beach Treasure Hunt Painters Hill Treasure Hunt Severn Grove Treasure Hunt Annapolis Roads Treasure Hunt Bywater Estates Treasure Hunt Bancroft Treasure Hunt Dulls Corner Treasure Hunt Westwinds Treasure Hunt Wetheridge Estates Treasure Hunt Eatons Landing Treasure Hunt Greenbriar Treasure Hunt Heritage Treasure Hunt Providence Cove Treasure Hunt Anchorage Treasure Hunt Robinwood Treasure Hunt West Annapolis Treasure Hunt Dreams Landing Treasure Hunt Parole Treasure Hunt Homewood Treasure Hunt Annapolis Overlook Treasure Hunt Browns Woods Treasure Hunt Beechwood On The Burley Treasure Hunt Martins Cove Farm Treasure Hunt Eastport Terrace Treasure Hunt Hickory Hills Treasure Hunt Lincoln Heights Treasure Hunt Truxton Heights Treasure Hunt Indian Hills Treasure Hunt Weems Creek Treasure Hunt Great Meadows Treasure Hunt Eastport Treasure Hunt Wilelinor Estates Treasure Hunt Forest Meadows Treasure Hunt Mariners Cove Treasure Hunt Elktonia Treasure Hunt Severnside Treasure Hunt Pines On Severn Treasure Hunt Market Quay Treasure Hunt Knightsbridge Treasure Hunt Riverview Manor Treasure Hunt Timber Creek Treasure Hunt Georgetown East Treasure Hunt Bay View Heights Treasure Hunt Ferry Farms Treasure Hunt Romar Estates Treasure Hunt Harness Woods Treasure Hunt Dellwood Treasure Hunt Round View Treasure Hunt Severn Forest Treasure Hunt Colony Hills Treasure Hunt Threemile Oak Corner Treasure Hunt Winchester Treasure Hunt Baytowne Village Treasure Hunt Bloomsbury Square Treasure Hunt Tyler Heights Treasure Hunt Harkness Creek Park Treasure Hunt Rundelac Farm Treasure Hunt Watergate Village Treasure Hunt West Woods Treasure Hunt Hidden Point Treasure Hunt Wardour Bluffs Treasure Hunt Hunt Meadows Treasure Hunt Victor Haven Treasure Hunt Mariners Point Treasure Hunt Captains Choice Treasure Hunt Captains Walk Treasure Hunt Winchester On The Severn Treasure Hunt Primrose Acres Treasure Hunt Annapolis Treasure Hunt Forest Villa Treasure Hunt The Village Treasure Hunt Browns Woods Villa Treasure Hunt The Ridings Treasure Hunt Naval Academy Treasure Hunt The Courtyards Treasure Hunt New Point Treasure Hunt Keys Farm Treasure Hunt Wardour Treasure Hunt Hillsmere Shores Treasure Hunt Bay Ridge Junction Treasure Hunt Wilshire Treasure Hunt Greenbriar Gardens Treasure Hunt Lindamoor On The Severn Treasure Hunt Admiral Heights Treasure Hunt Loretta Heights Treasure Hunt

Escape Room

Lands End Escape Room Romar Estates Escape Room Bancroft Escape Room Manresa Escape Room Eastport Terrace Escape Room The Courtyards Escape Room Bywater Estates Escape Room Bembe Beach Escape Room Admiral Heights Escape Room Martins Cove Farm Escape Room Market Quay Escape Room Severn Forest Escape Room The Meadows Escape Room Bestgate Terrace Escape Room Bay Ridge Junction Escape Room Knightsbridge Escape Room Mariners Cove Escape Room Providence Cove Escape Room Painters Hill Escape Room Luce Creek Escape Room Indian Hills Escape Room Winchester On The Severn Escape Room Winchester Escape Room Brice Manor Escape Room Wardour Bluffs Escape Room Hillsmere Shores Escape Room Greenbriar Gardens Escape Room Truxton Heights Escape Room New Point Escape Room Forest Villa Escape Room Rundelac Farm Escape Room Loretta Heights Escape Room Browns Woods Escape Room Primrose Acres Escape Room Riverview Manor Escape Room Elktonia Escape Room Annapolis Escape Room Baytowne Village Escape Room Anchorage Escape Room Watergate Village Escape Room Timber Creek Escape Room Wetheridge Estates Escape Room Captains Choice Escape Room Wardour Escape Room Sturbridge Escape Room West Annapolis Escape Room Round View Escape Room West Woods Escape Room The Ridings Escape Room Greenbriar Escape Room Cedarwood Cove Escape Room Browns Woods Villa Escape Room Dreams Landing Escape Room Lindamoor On The Severn Escape Room The Village Escape Room Harkness Creek Park Escape Room Harness Woods Escape Room Ferry Farms Escape Room Gentry Escape Room Robinwood Escape Room Dulls Corner Escape Room Wilelinor Estates Escape Room Providence Historical Escape Room Colonial Manor Estates Escape Room Keys Farm Escape Room Severnside Escape Room Bloomsbury Square Escape Room Town Home Village Escape Room Mariners Point Escape Room Old Annapolis Neck Escape Room Pines On Severn Escape Room Beechwood On The Burley Escape Room Severn Grove Escape Room Pendennis Mount Escape Room Bay View Heights Escape Room Annapolis Roads Escape Room Threemile Oak Corner Escape Room Hickory Hills Escape Room Colony Hills Escape Room Eastport Escape Room Hidden Point Escape Room Heritage Escape Room Parole Escape Room Georgetown East Escape Room Forest Meadows Escape Room Dellwood Escape Room Naval Academy Escape Room Victor Haven Escape Room Tyler Heights Escape Room Homewood Escape Room Great Meadows Escape Room Eatons Landing Escape Room Annapolis Overlook Escape Room Wilshire Escape Room Dorsey Heights Escape Room Westwinds Escape Room Captains Walk Escape Room Hunt Meadows Escape Room Lincoln Heights Escape Room Weems Creek Escape Room

Amazing Race

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Scavenger Hunt

Admiral Heights Scavenger Hunt Great Meadows Scavenger Hunt Timber Creek Scavenger Hunt Riverview Manor Scavenger Hunt Beechwood On The Burley Scavenger Hunt The Courtyards Scavenger Hunt Winchester Scavenger Hunt Severn Forest Scavenger Hunt Threemile Oak Corner Scavenger Hunt Market Quay Scavenger Hunt Bembe Beach Scavenger Hunt Loretta Heights Scavenger Hunt West Annapolis Scavenger Hunt Wardour Scavenger Hunt Providence Historical Scavenger Hunt Wardour Bluffs Scavenger Hunt Knightsbridge Scavenger Hunt Captains Walk Scavenger Hunt Eastport Terrace Scavenger Hunt Indian Hills Scavenger Hunt The Ridings Scavenger Hunt Keys Farm Scavenger Hunt Robinwood Scavenger Hunt Wilelinor Estates Scavenger Hunt Naval Academy Scavenger Hunt West Woods Scavenger Hunt Lands End Scavenger Hunt Colony Hills Scavenger Hunt Wilshire Scavenger Hunt Browns Woods Villa Scavenger Hunt Hidden Point Scavenger Hunt The Meadows Scavenger Hunt Old Annapolis Neck Scavenger Hunt Captains Choice Scavenger Hunt Colonial Manor Estates Scavenger Hunt Harkness Creek Park Scavenger Hunt Bestgate Terrace Scavenger Hunt Dreams Landing Scavenger Hunt Parole Scavenger Hunt Painters Hill Scavenger Hunt Severnside Scavenger Hunt Ferry Farms Scavenger Hunt Hickory Hills Scavenger Hunt Providence Cove Scavenger Hunt Anchorage Scavenger Hunt Brice Manor Scavenger Hunt Westwinds Scavenger Hunt Truxton Heights Scavenger Hunt Browns Woods Scavenger Hunt Rundelac Farm Scavenger Hunt Bay Ridge Junction Scavenger Hunt Georgetown East Scavenger Hunt Romar Estates Scavenger Hunt Martins Cove Farm Scavenger Hunt Severn Grove Scavenger Hunt Forest Villa Scavenger Hunt Greenbriar Scavenger Hunt Tyler Heights Scavenger Hunt Bancroft Scavenger Hunt Wetheridge Estates Scavenger Hunt Heritage Scavenger Hunt Elktonia Scavenger Hunt Weems Creek Scavenger Hunt Annapolis Roads Scavenger Hunt Bywater Estates Scavenger Hunt New Point Scavenger Hunt Greenbriar Gardens Scavenger Hunt Dorsey Heights Scavenger Hunt Eatons Landing Scavenger Hunt Forest Meadows Scavenger Hunt Baytowne Village Scavenger Hunt Dellwood Scavenger Hunt Gentry Scavenger Hunt Watergate Village Scavenger Hunt Hillsmere Shores Scavenger Hunt Annapolis Scavenger Hunt Bay View Heights Scavenger Hunt Bloomsbury Square Scavenger Hunt Primrose Acres Scavenger Hunt Hunt Meadows Scavenger Hunt Mariners Point Scavenger Hunt Manresa Scavenger Hunt Luce Creek Scavenger Hunt Eastport Scavenger Hunt Cedarwood Cove Scavenger Hunt Town Home Village Scavenger Hunt Pines On Severn Scavenger Hunt Mariners Cove Scavenger Hunt Sturbridge Scavenger Hunt Lindamoor On The Severn Scavenger Hunt Round View Scavenger Hunt Lincoln Heights Scavenger Hunt Annapolis Overlook Scavenger Hunt Homewood Scavenger Hunt Victor Haven Scavenger Hunt Harness Woods Scavenger Hunt Winchester On The Severn Scavenger Hunt Pendennis Mount Scavenger Hunt Dulls Corner Scavenger Hunt The Village Scavenger Hunt

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