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

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

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.

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 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 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 ©

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Puzzling Adventures Highlights

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

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Some of the benefits of time spent outside can include improvements in sleep, blood pressure, cognitive function and physical activity, as well as reduced risks of chronic disease, such as type 2 diabetes, cardiovascular disease and cancer.

Harvard University

https://www.hsph.harvard.edu/news/hsph-in-the-news/spend-time-outdoors-itll-improve-your-health-say-experts/

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Rendering Map

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directions

60 State St, Boston, MA 02109

More Information

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Directory

Treasure Hunt

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

Scavenger Hunt

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

Walking Tour

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

Amazing Race

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

Escape Room

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

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