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 © Spicy jalapenos

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Puzzling Adventures Highlights

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

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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

Amazing Race

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

Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

Walking Tour

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

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