Walking Tour near Winter Hill, Massachusetts

Immerse yourself in the captivating realm of Puzzling Adventures, where self-guided tours merge seamlessly with interactive puzzles and questions. Reveal the city's secrets while sharpening your mental acuity. Enjoy urban exploration with a twist!

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 © Z Beanie

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Puzzling Adventures Highlights

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

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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

Treasure Hunt

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

Scavenger Hunt

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

Escape Room

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

Amazing Race

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

Walking Tour

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

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