Amazing Race near Winthrop Highlands, Massachusetts

Are you ready to race like the competitors on the Amazing Race? Assemble your team and prepare for a heart-pounding adventure through the city, solving riddles and chasing clues to victory. On our Puzzling Adventures leaderboard, only the swiftest and cleverest prevail!

Embark on a thrilling adventure through Boston! Unravel mysteries of the American Revolution, learn about the Boston Massacre, and the city's seafaring tradition. Discover iconic landmarks like Norman B. Leventhal Park and Rose Fitzgerald Kennedy Greenway. Uncover the secrets of Boston Harbor and its islands. Test your knowledge with intriguing questions about historical events, famous personalities, and much more. Don't forget to capture memories with your camera!

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About Puzzling Adventures

Are you ready for a fun outdoor activity with your family, friends, or a special someone?

Embark on a Puzzling Adventure, a combintation of scavenger hunt, amazing race, and self-guided tour. Immerse yourself in this one-of-a-kind outdoor experience, discovering city sights in an exciting new way. Traverse the route by answering questions or solving riddles. All that's required is your mobile device and your desire to enjoy an unforgettable journey!

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 Winthrop Highlands

What are people saying about Puzzling Adventures?

Customer Reviews

Had a lot of fun walking around, answering questions and being silly!

Eric G.

Really enjoyed learning things we didn't know about the history and culture of the city.

Dianne M.

We had so much fun we can't wait to try another adventure. Such a fun family activity and a great way to see the city.

Sandi K.

Image © Spicy jalapenos

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Puzzling Adventures Highlights

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

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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

Boston Self-Guided Scavenger Hunt, 1 Devonshire Pl, Boston, MA 02109

More Information

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Directory

Amazing Race

Ten Hills Amazing Race Aberdeen Amazing Race Squantum Amazing Race Uphams Corner Amazing Race Neponset Amazing Race Brookline Village Amazing Race Point Shirley Amazing Race Spring Hill Amazing Race North Brighton Amazing Race Beachmont Amazing Race Chelsea Amazing Race Court Park Amazing Race Brighton Amazing Race Crescent Beach Amazing Race Back Bay Amazing Race Ashmont Amazing Race Charlestown Amazing Race Old Cambridge Amazing Race Orient Heights Amazing Race Medford Amazing Race Jeffries Point Amazing Race Somerville Amazing Race Dorchester Amazing Race Coolidge Corner Amazing Race Quincy Market Amazing Race Winthrop Amazing Race Roxbury Amazing Race East Somerville Amazing Race Admirals Hill Amazing Race West End Amazing Race Dock Square Amazing Race Hendersonville Amazing Race South Bay Amazing Race Mount Auburn Amazing Race Wellington Amazing Race South End Amazing Race Allston Amazing Race Grove Hall Amazing Race Bay Village Amazing Race Savin Hill Amazing Race Cottage Park Amazing Race Forest Hills Amazing Race Boston Amazing Race Prospect Hill Amazing Race South Boston Amazing Race Cambridgeport Amazing Race Suffolk Downs Station Amazing Race Roxbury Crossing Amazing Race Waterfront Amazing Race Mount Bowdoin Amazing Race Jamaica Plain Amazing Race Winter Hill Amazing Race Mission Hill Amazing Race Brookline Amazing Race West Everett Amazing Race Beacon Hill Amazing Race North End Amazing Race Coolidge Hill Amazing Race Everett Amazing Race East Cambridge Amazing Race Mount Ida Amazing Race West Somerville Amazing Race North Cambridge Amazing Race Malden Centre Amazing Race Beaconsfield Amazing Race Huron Village Amazing Race Edgeworth Amazing Race Medford Hillside Amazing Race Sommerville Amazing Race Reservoir Amazing Race Va Boston Healthcare System Brockton Campus Amazing Race Malden Amazing Race Allston/brighton Amazing Race Longwood Station Amazing Race New Squantum Amazing Race Revere Amazing Race City Point Amazing Race Glendale Amazing Race Forest Hills Amazing Race Cambridge Amazing Race Kendall Square Amazing Race Inner Belt Amazing Race Winthrop Highlands Amazing Race Faulkner Amazing Race Downtown Financial District Amazing Race Dorchester North Amazing Race Strawberry Hill Amazing Race Winthrop Beach Amazing Race Avon Hill Amazing Race Fields Corner Amazing Race Dorchester Center Amazing Race Larchwood Amazing Race Meeting House Hill Amazing Race Cottage Hill Amazing Race Glenwood Amazing Race East Boston Amazing Race Downtown Boston Amazing Race Fenway/kenmore Amazing Race Fort Winthrop Historical Amazing Race Chinatown/leather District Amazing Race

Escape Room

Orient Heights Escape Room Roxbury Escape Room Downtown Financial District Escape Room South End Escape Room Hendersonville Escape Room Quincy Market Escape Room Medford Escape Room Forest Hills Escape Room Waterfront Escape Room South Bay Escape Room Winthrop Escape Room Chelsea Escape Room North End Escape Room Crescent Beach Escape Room Spring Hill Escape Room Cambridgeport Escape Room New Squantum Escape Room Winthrop Highlands Escape Room Meeting House Hill Escape Room Reservoir Escape Room Charlestown Escape Room East Cambridge Escape Room Downtown Boston Escape Room Inner Belt Escape Room Revere Escape Room Beaconsfield Escape Room Va Boston Healthcare System Brockton Campus Escape Room Faulkner Escape Room Malden Centre Escape Room Court Park Escape Room Somerville Escape Room Fields Corner Escape Room Glendale Escape Room Aberdeen Escape Room Glenwood Escape Room Edgeworth Escape Room East Boston Escape Room Strawberry Hill Escape Room North Brighton Escape Room Grove Hall Escape Room Beacon Hill Escape Room Sommerville Escape Room Ashmont Escape Room Uphams Corner Escape Room Huron Village Escape Room Chinatown/leather District Escape Room West Everett Escape Room Dorchester Center Escape Room Wellington Escape Room Avon Hill Escape Room Mount Ida Escape Room Forest Hills Escape Room Winthrop Beach Escape Room North Cambridge Escape Room Larchwood Escape Room Mission Hill Escape Room Allston/brighton Escape Room City Point Escape Room Winter Hill Escape Room Ten Hills Escape Room Boston Escape Room Savin Hill Escape Room Fort Winthrop Historical Escape Room Cambridge Escape Room Back Bay Escape Room Squantum Escape Room Cottage Hill Escape Room West Somerville Escape Room West End Escape Room Allston Escape Room Cottage Park Escape Room South Boston Escape Room Roxbury Crossing Escape Room Admirals Hill Escape Room East Somerville Escape Room Brighton Escape Room Jeffries Point Escape Room Coolidge Corner Escape Room Neponset Escape Room Mount Bowdoin Escape Room Malden Escape Room Fenway/kenmore Escape Room Beachmont Escape Room Jamaica Plain Escape Room Medford Hillside Escape Room Brookline Escape Room Brookline Village Escape Room Longwood Station Escape Room Coolidge Hill Escape Room Dorchester Escape Room Prospect Hill Escape Room Dorchester North Escape Room Bay Village Escape Room Suffolk Downs Station Escape Room Point Shirley Escape Room Dock Square Escape Room Everett Escape Room Old Cambridge Escape Room Mount Auburn Escape Room Kendall Square Escape Room

Treasure Hunt

Hendersonville Treasure Hunt City Point Treasure Hunt Everett Treasure Hunt Kendall Square Treasure Hunt North End Treasure Hunt North Cambridge Treasure Hunt Forest Hills Treasure Hunt Court Park Treasure Hunt Jamaica Plain Treasure Hunt Glenwood Treasure Hunt Chinatown/leather District Treasure Hunt Huron Village Treasure Hunt Spring Hill Treasure Hunt Crescent Beach Treasure Hunt Brighton Treasure Hunt Beacon Hill Treasure Hunt Sommerville Treasure Hunt Cambridge Treasure Hunt Squantum Treasure Hunt Admirals Hill Treasure Hunt Cottage Park Treasure Hunt Avon Hill Treasure Hunt Fields Corner Treasure Hunt Wellington Treasure Hunt Meeting House Hill Treasure Hunt Winthrop Treasure Hunt Dock Square Treasure Hunt Somerville Treasure Hunt Edgeworth Treasure Hunt Fort Winthrop Historical Treasure Hunt Downtown Boston Treasure Hunt Downtown Financial District Treasure Hunt South Boston Treasure Hunt Winter Hill Treasure Hunt Reservoir Treasure Hunt Mount Ida Treasure Hunt Savin Hill Treasure Hunt South Bay Treasure Hunt Mount Auburn Treasure Hunt Uphams Corner Treasure Hunt Malden Treasure Hunt Fenway/kenmore Treasure Hunt Jeffries Point Treasure Hunt West End Treasure Hunt Grove Hall Treasure Hunt Medford Treasure Hunt Medford Hillside Treasure Hunt Dorchester Center Treasure Hunt Forest Hills Treasure Hunt New Squantum Treasure Hunt Mission Hill Treasure Hunt Allston Treasure Hunt Orient Heights Treasure Hunt Longwood Station Treasure Hunt Waterfront Treasure Hunt Roxbury Crossing Treasure Hunt Neponset Treasure Hunt Va Boston Healthcare System Brockton Campus Treasure Hunt South End Treasure Hunt Allston/brighton Treasure Hunt Point Shirley Treasure Hunt Dorchester Treasure Hunt Aberdeen Treasure Hunt Larchwood Treasure Hunt Beachmont Treasure Hunt Charlestown Treasure Hunt Chelsea Treasure Hunt Inner Belt Treasure Hunt Ashmont Treasure Hunt Coolidge Hill Treasure Hunt Mount Bowdoin Treasure Hunt West Everett Treasure Hunt Winthrop Beach Treasure Hunt East Somerville Treasure Hunt Faulkner Treasure Hunt West Somerville Treasure Hunt Ten Hills Treasure Hunt Suffolk Downs Station Treasure Hunt Brookline Village Treasure Hunt Roxbury Treasure Hunt Beaconsfield Treasure Hunt Revere Treasure Hunt Cambridgeport Treasure Hunt Quincy Market Treasure Hunt Malden Centre Treasure Hunt Boston Treasure Hunt Coolidge Corner Treasure Hunt Prospect Hill Treasure Hunt Winthrop Highlands Treasure Hunt North Brighton Treasure Hunt Strawberry Hill Treasure Hunt Bay Village Treasure Hunt East Boston Treasure Hunt East Cambridge Treasure Hunt Back Bay Treasure Hunt Brookline Treasure Hunt Cottage Hill Treasure Hunt Dorchester North Treasure Hunt Glendale Treasure Hunt Old Cambridge Treasure Hunt

Walking Tour

Meeting House Hill Walking Tour Bay Village Walking Tour Dock Square Walking Tour Revere Walking Tour Winthrop Highlands Walking Tour Mission Hill Walking Tour Boston Walking Tour City Point Walking Tour Jeffries Point Walking Tour Dorchester North Walking Tour Court Park Walking Tour North Cambridge Walking Tour Orient Heights Walking Tour West End Walking Tour Cottage Park Walking Tour Uphams Corner Walking Tour Suffolk Downs Station Walking Tour Admirals Hill Walking Tour Brookline Walking Tour Prospect Hill Walking Tour Faulkner Walking Tour Fields Corner Walking Tour New Squantum Walking Tour Mount Bowdoin Walking Tour Chinatown/leather District Walking Tour Downtown Financial District Walking Tour Beaconsfield Walking Tour Edgeworth Walking Tour Dorchester Center Walking Tour Neponset Walking Tour Ten Hills Walking Tour Quincy Market Walking Tour Beachmont Walking Tour Medford Walking Tour Cambridgeport Walking Tour West Everett Walking Tour Larchwood Walking Tour Jamaica Plain Walking Tour Avon Hill Walking Tour Forest Hills Walking Tour Crescent Beach Walking Tour Dorchester Walking Tour Squantum Walking Tour Wellington Walking Tour North Brighton Walking Tour Malden Centre Walking Tour Mount Auburn Walking Tour Charlestown Walking Tour Glendale Walking Tour Coolidge Corner Walking Tour Mount Ida Walking Tour Savin Hill Walking Tour South Boston Walking Tour Medford Hillside Walking Tour Grove Hall Walking Tour Sommerville Walking Tour Back Bay Walking Tour Fort Winthrop Historical Walking Tour Ashmont Walking Tour Beacon Hill Walking Tour Malden Walking Tour Everett Walking Tour South Bay Walking Tour South End Walking Tour Old Cambridge Walking Tour Kendall Square Walking Tour Point Shirley Walking Tour North End Walking Tour Aberdeen Walking Tour Reservoir Walking Tour East Cambridge Walking Tour Roxbury Crossing Walking Tour Cottage Hill Walking Tour Glenwood Walking Tour Waterfront Walking Tour Strawberry Hill Walking Tour Forest Hills Walking Tour Cambridge Walking Tour Downtown Boston Walking Tour East Boston Walking Tour Brookline Village Walking Tour Inner Belt Walking Tour East Somerville Walking Tour Somerville Walking Tour Winthrop Beach Walking Tour Winthrop Walking Tour Va Boston Healthcare System Brockton Campus Walking Tour Chelsea Walking Tour West Somerville Walking Tour Longwood Station Walking Tour Allston/brighton Walking Tour Coolidge Hill Walking Tour Roxbury Walking Tour Allston Walking Tour Hendersonville Walking Tour Huron Village Walking Tour Brighton Walking Tour Fenway/kenmore Walking Tour Winter Hill Walking Tour Spring Hill Walking Tour

Scavenger Hunt

Glenwood Scavenger Hunt Winter Hill Scavenger Hunt Allston Scavenger Hunt Coolidge Corner Scavenger Hunt Prospect Hill Scavenger Hunt North Cambridge Scavenger Hunt Huron Village Scavenger Hunt Dorchester Center Scavenger Hunt Beaconsfield Scavenger Hunt South Boston Scavenger Hunt North Brighton Scavenger Hunt Winthrop Highlands Scavenger Hunt Strawberry Hill Scavenger Hunt Squantum Scavenger Hunt Roxbury Crossing Scavenger Hunt Chinatown/leather District Scavenger Hunt Coolidge Hill Scavenger Hunt West Everett Scavenger Hunt Mission Hill Scavenger Hunt Avon Hill Scavenger Hunt Sommerville Scavenger Hunt Fort Winthrop Historical Scavenger Hunt Somerville Scavenger Hunt Cambridgeport Scavenger Hunt Downtown Financial District Scavenger Hunt Roxbury Scavenger Hunt Cottage Park Scavenger Hunt Admirals Hill Scavenger Hunt Malden Centre Scavenger Hunt Aberdeen Scavenger Hunt Larchwood Scavenger Hunt Forest Hills Scavenger Hunt Brookline Scavenger Hunt Ashmont Scavenger Hunt Va Boston Healthcare System Brockton Campus Scavenger Hunt Reservoir Scavenger Hunt Mount Auburn Scavenger Hunt New Squantum Scavenger Hunt Mount Ida Scavenger Hunt Boston Scavenger Hunt Meeting House Hill Scavenger Hunt Faulkner Scavenger Hunt Inner Belt Scavenger Hunt Revere Scavenger Hunt Jamaica Plain Scavenger Hunt Hendersonville Scavenger Hunt Point Shirley Scavenger Hunt Dorchester Scavenger Hunt Uphams Corner Scavenger Hunt Brighton Scavenger Hunt Jeffries Point Scavenger Hunt West Somerville Scavenger Hunt Charlestown Scavenger Hunt City Point Scavenger Hunt West End Scavenger Hunt Edgeworth Scavenger Hunt Wellington Scavenger Hunt Malden Scavenger Hunt South End Scavenger Hunt Forest Hills Scavenger Hunt Brookline Village Scavenger Hunt Fenway/kenmore Scavenger Hunt Suffolk Downs Station Scavenger Hunt Quincy Market Scavenger Hunt Grove Hall Scavenger Hunt Mount Bowdoin Scavenger Hunt Downtown Boston Scavenger Hunt South Bay Scavenger Hunt Crescent Beach Scavenger Hunt Cambridge Scavenger Hunt Dorchester North Scavenger Hunt North End Scavenger Hunt Glendale Scavenger Hunt Beacon Hill Scavenger Hunt Orient Heights Scavenger Hunt Cottage Hill Scavenger Hunt East Cambridge Scavenger Hunt Savin Hill Scavenger Hunt Back Bay Scavenger Hunt Fields Corner Scavenger Hunt Neponset Scavenger Hunt Bay Village Scavenger Hunt Kendall Square Scavenger Hunt Medford Scavenger Hunt Longwood Station Scavenger Hunt Spring Hill Scavenger Hunt Winthrop Beach Scavenger Hunt Medford Hillside Scavenger Hunt Dock Square Scavenger Hunt Beachmont Scavenger Hunt East Somerville Scavenger Hunt Allston/brighton Scavenger Hunt Ten Hills Scavenger Hunt Winthrop Scavenger Hunt Everett Scavenger Hunt Chelsea Scavenger Hunt Waterfront Scavenger Hunt Court Park Scavenger Hunt East Boston Scavenger Hunt Old Cambridge Scavenger Hunt

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