Amazing Race near Winter Hill, Massachusetts

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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!

Embark on a thrilling journey in Boston! Unravel the city's secrets, from its early European settlers to its modern-day marvels. Answer intriguing questions, snap team selfies, and learn about the city's rich history. Discover the oldest city park in the U.S., explore the subway's electrifying past, and marvel at a 19-ton sculpture. Uncover the city's football roots, its driving laws, and its stunning public garden. You'll even get a taste of Broadway with a Hamilton trivia!

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About Puzzling Adventures

Are you ready for a fun outdoor activity with your family, friends, or a special someone?

Embark on a Puzzling Adventure, a combintation of scavenger hunt, amazing race, and self-guided tour. Immerse yourself in this one-of-a-kind outdoor experience, discovering city sights in an exciting new way. Traverse the route by answering questions or solving riddles. All that's required is your mobile device and your desire to enjoy an unforgettable journey!

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.

Embark on your journey, your way, your time...

As 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 pace.

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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.

Really enjoyed learning things we didn't know about the history and culture of the city.

Dianne M.

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 © The VC Incredibles

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Puzzling Adventures Highlights

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

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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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directions

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

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Directory

Walking Tour

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

Amazing Race

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

Escape Room

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

Scavenger Hunt

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

Treasure Hunt

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

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