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 © Bowers33

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Puzzling Adventures Highlights

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

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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

Scavenger Hunt

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

Escape Room

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

Treasure Hunt

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

Walking Tour

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

Amazing Race

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

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