Amazing Race near Winthrop Highlands, Massachusetts

Calling all Amazing Race enthusiasts! Team up with your fellow adventurers for a fast-paced quest around the city, deciphering questions and piecing together your answers along the way. Can you outsmart the competition and clinch the top spot on our Puzzling Adventures leaderboard?

Embark on a thrilling quest around Boston! Uncover the city's secrets, from its early European settlers to its iconic landmarks. Test your knowledge with intriguing questions, snap memorable photos, and learn fascinating facts about Boston's history. From the oldest city park in the U.S. to the first public botanical garden, there's a surprise at every turn. Don't forget to look out for bonus points and remember, every second counts! Ready for an adventure? Boston awaits!

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About Puzzling Adventures

Looking for things to do with your date, friends, kids, teenagers, or other family?

Puzzling Adventures are a cross between a scavenger hunt, an amazing race, and a self-guided walking tour. Enjoy this unique outdoor activity and experience sightseeing in a fun new way. Each city route consists of a series of locations that you are guided to where you answer questions or solve puzzles to receive your next instruction. All you need is your own mobile device with a data connection.

Fun for all ages...

Kids, teens, tweens, young adults, seniors, groups, couples, or individuals. Almost all of our adventures are designed to be wheelchair and stroller friendly and all are carefully crafted to be entertaining and informative with something to appeal to everyone.

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 Winthrop Highlands

What are people saying about Puzzling Adventures?

Customer Reviews

Highly recommend to anyone for a fun day out in the city!

Molly C.

This was really fun, it was a nice day and we learned a lot!

Bill 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 © Sierras uncles orange shirt

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Puzzling Adventures Highlights

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

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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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Mapping Boston Self-Guided Scavenger Hunt, 73 Tremont St., Boston, MA 02108

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directions

Boston Self-Guided Scavenger Hunt, 73 Tremont St., Boston, MA 02108

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Directory

Walking Tour

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

Amazing Race

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

Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

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