Amazing Race near Winter Hill, Massachusetts

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If you love the thrill of the Amazing Race, gather your teammates for an adrenaline-fueled dash across the city, tackling questions and hunting for clues. To claim the coveted top spot on our Puzzling Adventures leaderboard, speed and smarts are your ultimate allies!

Embark on a whirlwind adventure through Boston's rich history! Uncover the secrets of the American Revolution, learn about the city's seafaring traditions, and even delve into the world of boxing. Snap selfies, answer trivia, and explore iconic sites like the Massachusetts State House. Discover the city's role in the slave trade, rum, fish, salt, and tobacco industries. Unearth fun facts like Boston's ban on Christmas celebrations in the 17th century. Ready, set, explore!

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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!

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.

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 © Los Jefes

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Puzzling Adventures Highlights

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

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Time in the outdoors offers the benefit of mental rest and rejuvenation, it has been shown to improve memory, attention, impulse control, and creativity in the general population. For example, in children, it has led to improved school performance.

McLean Hospital

https://www.mcleanhospital.org/essential/nature

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Rendering Map

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directions

Boston Self-Guided Scavenger Hunt, 60 State St, Boston, MA 02109

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Directory

Scavenger Hunt

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

Treasure Hunt

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

Walking Tour

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

Amazing Race

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Escape Room

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

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