Walking Tour near Winter Hill, Massachusetts

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.

Puzzling Adventures

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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!

Suitable for all ages...

From grandkids to grandparents, our adventures are designed to entertain and engage everyone. With careful consideration for accessibility, almost all of our experiences are wheelchair and stroller friendly. Each adventure is curated to provide a mix of entertainment and enlightenment, ensuring there's something for every member of your group.

Adventure at your own convenience...

With our self-guided experiences, there's no need to book ahead, just play whenever you like! Whether you're vying for victory or enjoying a leisurely day out, you set the pace. Indulge your senses in the various locales you'll discover, soaking in the ambiance at your own speed.

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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.

Fun fun fun! great way to experience a new area!

Rhonda R.

We had a great time. Great bonding experience for the whole family.

Angie B.

Image © Z Beanie

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Puzzling Adventures Highlights

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

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Time in the outdoors offers the benefit of mental rest and rejuvenation, it has been shown to improve memory, attention, impulse control, and creativity in the general population. For example, in children, it has led to improved school performance.

McLean Hospital

https://www.mcleanhospital.org/essential/nature

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Mapping 65 John F Kennedy St, Cambridge, MA 02138

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directions

65 John F Kennedy St, Cambridge, MA 02138

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Directory

Treasure Hunt

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

Escape Room

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

Walking Tour

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

Amazing Race

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

Scavenger Hunt

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

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