Amazing Race near Winter Hill, 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!

Puzzling Adventures

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About Puzzling Adventures

Searching for an engaging activity to enjoy with your kids, teens, tweens, other family, friends or colleagues?

Step into the world of Puzzling Adventures, a captivating blend of scavenger hunt, self-guided walking tour and an amazing race. Experience the outdoors in a whole new light as you embark on this unique adventure. Navigate the city, solving puzzles and answering questions to uncover your next destination. All you need is a smartphone and an appetite for an unforgettable escapade!

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.

Flexibility to explore at your own tempo...

Thanks to our self-guided adventures, scheduling is a breeze, no reservations required. Whether you're aiming for the top spot or opting for a more relaxed journey, it's entirely up to you. Take the time to dive deeper into each destination or race to be number one, the choice is yours!

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Puzzling Adventures near Winter Hill

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!

Lynne-Marie A.

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

Bill S.

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 © Sparkling Seas

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Puzzling Adventures Highlights

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

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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

65 John F Kennedy St, Cambridge, MA 02138

More Information

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Directory

Walking Tour

Somerville Walking Tour Dorchester North Walking Tour Wedgemere Walking Tour Waverley Walking Tour Boston Walking Tour West Medford Walking Tour Thompsonville Walking Tour Va Boston Healthcare System Brockton Campus Walking Tour Jeffries Point Walking Tour Arlington Walking Tour Glendale Walking Tour Chelsea Walking Tour Mission Hill Walking Tour Watertown Walking Tour Ten Hills Walking Tour Newton Center Walking Tour Brighton Walking Tour North Cambridge Walking Tour Old Cambridge Walking Tour East Arlington Walking Tour Malden Walking Tour Prospect Hill Walking Tour Roxbury Walking Tour Inner Belt Walking Tour East Boston Walking Tour Chinatown/leather District Walking Tour Brookline Village Walking Tour Quincy Market Walking Tour Avon Hill Walking Tour Mount Auburn Walking Tour West Somerville Walking Tour Larchwood Walking Tour Everett Walking Tour Brookline Walking Tour Edgeworth Walking Tour Roxbury Crossing Walking Tour Bemis Walking Tour Charlestown Walking Tour North Brighton Walking Tour Beaconsfield Walking Tour Dock Square Walking Tour Sommerville Walking Tour Fenway/kenmore Walking Tour Longwood Station Walking Tour Chestnut Hill Walking Tour Malden Centre Walking Tour Jamaica Plain Walking Tour Eastview Park Walking Tour Cambridgeport Walking Tour Back Bay Walking Tour Cambridge Walking Tour Wellington Walking Tour Clematis Brook Station Walking Tour Allston Brighton Walking Tour Arlington Heights Walking Tour Beacon Hill Walking Tour West End Walking Tour Coolidge Hill Walking Tour Newton Walking Tour North End Walking Tour Symmes Corner Walking Tour Bay Village Walking Tour Waterfront Walking Tour West Everett Walking Tour Downtown/financial District Walking Tour Oak Grove Walking Tour Brattle Walking Tour Uphams Corner Walking Tour Newtonville Walking Tour Downtown Boston Walking Tour Grove Hall Walking Tour Beaver Brook Station Walking Tour Aberdeen Walking Tour Medford Hillside Walking Tour Payson Park Walking Tour South Boston Walking Tour North Village Walking Tour South Bay Walking Tour Spring Hill Walking Tour East Watertown Walking Tour Belmont Walking Tour Cedar Hill Camp Walking Tour Reservoir Walking Tour Strawberry Hill Walking Tour South End Walking Tour Faneuil Walking Tour East Somerville Walking Tour Newton Corner Walking Tour Coolidge Corner Walking Tour Hendersonville Walking Tour Kendall Square Walking Tour Medford Walking Tour Admirals Hill Walking Tour Malden Highlands Walking Tour Winter Hill Walking Tour Allston Walking Tour Nonantum Walking Tour East Cambridge Walking Tour Glenwood Walking Tour Huron Village Walking Tour

Scavenger Hunt

Waterfront Scavenger Hunt Downtown Boston Scavenger Hunt Edgeworth Scavenger Hunt Dock Square Scavenger Hunt Charlestown Scavenger Hunt Belmont Scavenger Hunt Brattle Scavenger Hunt North Cambridge Scavenger Hunt Quincy Market Scavenger Hunt Winter Hill Scavenger Hunt Bay Village Scavenger Hunt Chestnut Hill Scavenger Hunt Downtown/financial District Scavenger Hunt Inner Belt Scavenger Hunt Watertown Scavenger Hunt Somerville Scavenger Hunt Wedgemere Scavenger Hunt West End Scavenger Hunt North Village Scavenger Hunt Jeffries Point Scavenger Hunt Coolidge Corner Scavenger Hunt Sommerville Scavenger Hunt Old Cambridge Scavenger Hunt Allston Brighton Scavenger Hunt Faneuil Scavenger Hunt West Everett Scavenger Hunt Ten Hills Scavenger Hunt West Medford Scavenger Hunt Cambridgeport Scavenger Hunt East Arlington Scavenger Hunt East Somerville Scavenger Hunt South Bay Scavenger Hunt Huron Village Scavenger Hunt Malden Scavenger Hunt Back Bay Scavenger Hunt Oak Grove Scavenger Hunt Newton Center Scavenger Hunt East Boston Scavenger Hunt Jamaica Plain Scavenger Hunt Roxbury Scavenger Hunt Payson Park Scavenger Hunt Everett Scavenger Hunt Va Boston Healthcare System Brockton Campus Scavenger Hunt Fenway/kenmore Scavenger Hunt West Somerville Scavenger Hunt Symmes Corner Scavenger Hunt Prospect Hill Scavenger Hunt Cedar Hill Camp Scavenger Hunt Allston Scavenger Hunt Longwood Station Scavenger Hunt Medford Scavenger Hunt Arlington Heights Scavenger Hunt Malden Highlands Scavenger Hunt Chelsea Scavenger Hunt Coolidge Hill Scavenger Hunt East Watertown Scavenger Hunt Dorchester North Scavenger Hunt Nonantum Scavenger Hunt Mount Auburn Scavenger Hunt Newton Corner Scavenger Hunt Newtonville Scavenger Hunt Aberdeen Scavenger Hunt Admirals Hill Scavenger Hunt Brookline Village Scavenger Hunt Mission Hill Scavenger Hunt Bemis Scavenger Hunt North End Scavenger Hunt Newton Scavenger Hunt Eastview Park Scavenger Hunt Beacon Hill Scavenger Hunt Kendall Square Scavenger Hunt South Boston Scavenger Hunt Spring Hill Scavenger Hunt Avon Hill Scavenger Hunt Beaconsfield Scavenger Hunt Beaver Brook Station Scavenger Hunt Glendale Scavenger Hunt Glenwood Scavenger Hunt Thompsonville Scavenger Hunt Clematis Brook Station Scavenger Hunt Chinatown/leather District Scavenger Hunt Hendersonville Scavenger Hunt Boston Scavenger Hunt Wellington Scavenger Hunt Brighton Scavenger Hunt Waverley Scavenger Hunt North Brighton Scavenger Hunt Reservoir Scavenger Hunt East Cambridge Scavenger Hunt Roxbury Crossing Scavenger Hunt Medford Hillside Scavenger Hunt Brookline Scavenger Hunt South End Scavenger Hunt Uphams Corner Scavenger Hunt Cambridge Scavenger Hunt Larchwood Scavenger Hunt Strawberry Hill Scavenger Hunt Arlington Scavenger Hunt Malden Centre Scavenger Hunt Grove Hall Scavenger Hunt

Treasure Hunt

Beaconsfield Treasure Hunt Faneuil Treasure Hunt East Arlington Treasure Hunt North End Treasure Hunt Bay Village Treasure Hunt Nonantum Treasure Hunt Bemis Treasure Hunt Chinatown/leather District Treasure Hunt Glendale Treasure Hunt Arlington Heights Treasure Hunt Fenway/kenmore Treasure Hunt North Brighton Treasure Hunt North Cambridge Treasure Hunt Newtonville Treasure Hunt Edgeworth Treasure Hunt Kendall Square Treasure Hunt Newton Treasure Hunt Brookline Treasure Hunt Cedar Hill Camp Treasure Hunt Aberdeen Treasure Hunt North Village Treasure Hunt South Bay Treasure Hunt East Cambridge Treasure Hunt Coolidge Corner Treasure Hunt Reservoir Treasure Hunt Symmes Corner Treasure Hunt Arlington Treasure Hunt Wellington Treasure Hunt Belmont Treasure Hunt Somerville Treasure Hunt Downtown Boston Treasure Hunt Huron Village Treasure Hunt Brattle Treasure Hunt Thompsonville Treasure Hunt South End Treasure Hunt Newton Center Treasure Hunt Roxbury Crossing Treasure Hunt Larchwood Treasure Hunt Inner Belt Treasure Hunt East Somerville Treasure Hunt Wedgemere Treasure Hunt Strawberry Hill Treasure Hunt Roxbury Treasure Hunt Spring Hill Treasure Hunt Dorchester North Treasure Hunt Longwood Station Treasure Hunt Waverley Treasure Hunt Medford Hillside Treasure Hunt Cambridgeport Treasure Hunt Beaver Brook Station Treasure Hunt Charlestown Treasure Hunt Waterfront Treasure Hunt Uphams Corner Treasure Hunt Allston Brighton Treasure Hunt Grove Hall Treasure Hunt Everett Treasure Hunt Beacon Hill Treasure Hunt Admirals Hill Treasure Hunt Mission Hill Treasure Hunt Cambridge Treasure Hunt Jeffries Point Treasure Hunt West Everett Treasure Hunt Medford Treasure Hunt Avon Hill Treasure Hunt Prospect Hill Treasure Hunt Ten Hills Treasure Hunt Brighton Treasure Hunt Chestnut Hill Treasure Hunt Payson Park Treasure Hunt Oak Grove Treasure Hunt Mount Auburn Treasure Hunt Old Cambridge Treasure Hunt Dock Square Treasure Hunt Watertown Treasure Hunt Jamaica Plain Treasure Hunt Malden Centre Treasure Hunt Downtown/financial District Treasure Hunt South Boston Treasure Hunt Sommerville Treasure Hunt West Somerville Treasure Hunt Glenwood Treasure Hunt Chelsea Treasure Hunt Va Boston Healthcare System Brockton Campus Treasure Hunt Hendersonville Treasure Hunt Eastview Park Treasure Hunt Coolidge Hill Treasure Hunt Boston Treasure Hunt East Watertown Treasure Hunt Allston Treasure Hunt Back Bay Treasure Hunt West End Treasure Hunt Quincy Market Treasure Hunt Brookline Village Treasure Hunt East Boston Treasure Hunt Newton Corner Treasure Hunt Malden Highlands Treasure Hunt Clematis Brook Station Treasure Hunt Winter Hill Treasure Hunt Malden Treasure Hunt West Medford Treasure Hunt

Amazing Race

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Escape Room

Larchwood Escape Room Bay Village Escape Room Watertown Escape Room Kendall Square Escape Room Waterfront Escape Room Bemis Escape Room Aberdeen Escape Room East Boston Escape Room Malden Highlands Escape Room Everett Escape Room East Somerville Escape Room South Bay Escape Room Brattle Escape Room Beaver Brook Station Escape Room Roxbury Escape Room West Everett Escape Room Spring Hill Escape Room Arlington Heights Escape Room Arlington Escape Room Newton Corner Escape Room Chelsea Escape Room North End Escape Room Coolidge Corner Escape Room Clematis Brook Station Escape Room Longwood Station Escape Room Quincy Market Escape Room Medford Escape Room Somerville Escape Room Malden Escape Room Ten Hills Escape Room Allston Brighton Escape Room West Somerville Escape Room East Arlington Escape Room Oak Grove Escape Room Prospect Hill Escape Room Mission Hill Escape Room East Cambridge Escape Room Beacon Hill Escape Room Fenway/kenmore Escape Room Hendersonville Escape Room North Brighton Escape Room Payson Park Escape Room Edgeworth Escape Room Inner Belt Escape Room Allston Escape Room Glendale Escape Room Newton Escape Room Glenwood Escape Room Reservoir Escape Room East Watertown Escape Room Downtown Boston Escape Room Jeffries Point Escape Room Strawberry Hill Escape Room Wellington Escape Room West End Escape Room North Village Escape Room Huron Village Escape Room Mount Auburn Escape Room Jamaica Plain Escape Room Newton Center Escape Room Belmont Escape Room Beaconsfield Escape Room Roxbury Crossing Escape Room Downtown/financial District Escape Room Grove Hall Escape Room Charlestown Escape Room Winter Hill Escape Room Cedar Hill Camp Escape Room Admirals Hill Escape Room Malden Centre Escape Room Avon Hill Escape Room West Medford Escape Room Brighton Escape Room Medford Hillside Escape Room Chinatown/leather District Escape Room North Cambridge Escape Room Nonantum Escape Room Boston Escape Room Cambridgeport Escape Room Eastview Park Escape Room Waverley Escape Room Cambridge Escape Room Old Cambridge Escape Room Coolidge Hill Escape Room Dock Square Escape Room South End Escape Room South Boston Escape Room Wedgemere Escape Room Brookline Village Escape Room Symmes Corner Escape Room Newtonville Escape Room Chestnut Hill Escape Room Uphams Corner Escape Room Faneuil Escape Room Back Bay Escape Room Sommerville Escape Room Thompsonville Escape Room Dorchester North Escape Room Va Boston Healthcare System Brockton Campus Escape Room Brookline Escape Room

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