Walking Tour near Annapolis Overlook, Maryland

Puzzling Adventures are part self-guided walking tour, part interactive game. Uncover hidden secrets of the city while exercising your mind as you explore the city from a completely new perspective.

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

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

Entertaining for all age groups...

Whether you're a grade-schooler, a young adult, or a senior, our adventures provide enjoyment for everyone. Almost all of our hand-crafted experiences are accessible to wheelchairs and strollers, prioritizing inclusivity. Each adventure is infused with elements of fun and learning, appealing to a wide range of interests and tastes.

Embark on your journey, your way, your time...

As our adventures are self-guided, you have the freedom to play whenever suits you with no need for reservations. Whether you're racing for first place or savoring each moment, the choice is yours. Immerse your senses in all of the locations you'll encounter, all at your own pace.

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Puzzling Adventures near Annapolis Overlook

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!

Lynne-Marie A.

Very enjoyable!

Kelly L.

I liked how each clue showed us little known facts about the city. It made finding local eateries and sights easy. Very fun!

Taylor V.

Image © Dennis Desiree Forever

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Puzzling Adventures Highlights

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

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Spending time outdoors can improve overall health and wellness. The outdoors offers many opportunities to be physically active. Time outdoors may also promote mental health and stress reduction.

Centers for Disease Control and Prevention

https://www.cdc.gov/cancer/skin/basic_info/outdoors.htm

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directions

25 Northwest St., Annapolis, MD 21401

More Information

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Directory

Scavenger Hunt

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

Escape Room

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

Walking Tour

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

Amazing Race

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

Treasure Hunt

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

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