Amazing Race near Winter Hill, Massachusetts

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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!

Embark on a thrilling adventure through Boston! Unravel mysteries of the American Revolution, learn about the Boston Massacre, and the city's seafaring tradition. Discover iconic landmarks like Norman B. Leventhal Park and Rose Fitzgerald Kennedy Greenway. Uncover the secrets of Boston Harbor and its islands. Test your knowledge with intriguing questions about historical events, famous personalities, and much more. Don't forget to capture memories with your camera!

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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.

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.

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 Winter Hill

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.

Had a blast! Would definitely do it again!

Candice B.

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 © Red Gables

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Puzzling Adventures Highlights

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

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Spending time outdoors can improve overall health and wellness. The outdoors offers many opportunities to be physically active. Time outdoors may also promote mental health and stress reduction.

Centers for Disease Control and Prevention

https://www.cdc.gov/cancer/skin/basic_info/outdoors.htm

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Rendering Map

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View Purchase Options

directions

Boston Self-Guided Scavenger Hunt, 1 Devonshire Pl, Boston, MA 02109

More Information

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Directory

Scavenger Hunt

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

Amazing Race

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

Treasure Hunt

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

Escape Room

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

Walking Tour

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

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