Amazing Race near Winter Hill, Massachusetts

Are you a fan of the Amazing Race? Grab some teammates and dash around the city while deciphering questions and searching for answers. You will need to be the quickest and the smartest to win top spot on our Puzzling Adventures leaderboard!

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 © Sparkling Seas

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Puzzling Adventures Highlights

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

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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

Walking Tour

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

Amazing Race

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

Scavenger Hunt

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

Escape Room

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

Treasure Hunt

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

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