Amazing Race near Winthrop Highlands, Massachusetts

Inspired by the excitement of the Amazing Race, rally your team for a high-speed pursuit through the city streets, decoding questions and hunting down clues. Only the quickest and sharpest minds will triumph and secure their place atop our Puzzling Adventures leaderboard!

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!

Perfect for all generations...

Whether you're spending special time with your friends, children, parents, grandchildren, or grandparents, our adventures are tailored to accommodate everyone. Our wheelchair and stroller-friendly experiences are crafted to be both entertaining and informative, appealing to a diverse audience. With activities designed to engage all ages, Puzzling Adventures goal is to provide a memorable experience for everybody who participates.

Play on your own schedule at your own pace...

Since our adventures are self-guided, you have the freedom to play whenever suits you with no need for reservations. Whether you're racing for first place or savoring each moment, the choice is yours. Immerse your senses in all of the locations you'll encounter, all at your own speed.

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Puzzling Adventures near Winthrop Highlands

What are people saying about Puzzling Adventures?

Customer Reviews

This scavenger hunt was great for the whole family. We had ages 3 to 63 on our team and we all had a wonderful time!

Karen B.

Amazing experience. Very well set up.

Melissa S.

I liked how each clue showed us little known facts about the city. It made finding local eateries and sights easy. Very fun!

Taylor V.

Image © Livroy 2025

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Puzzling Adventures Highlights

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

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Hundreds of studies have linked spending time outside to better health outcomes like decreases in incidences of diabetes and cardio-vascular mortality, lower blood pressure and heart rate, and better immune system function. In fact, these positive effects that are so well-documented that more and more doctors are issuing 'nature prescriptions' to help treat a range of conditions from heart disease, hypertension, high cholesterol, and diabetes, to chronic stress, depression and anxiety, insomnia and even PTSD.

Forbes

https://www.forbes.com/sites/cassidyrandall/2020/04/09/why-going-outside-is-good-for-your-health-especially-right-now/?sh=18e3c6382de9

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directions

73 Tremont St., Boston, MA 02108

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More Information

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Directory

Treasure Hunt

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

Scavenger Hunt

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

Amazing Race

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

Escape Room

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

Walking Tour

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

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