Amazing Race near Winter Hill, Massachusetts

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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

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

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.

Play on your own schedule at your own pace...

Since 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 speed.

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Puzzling Adventures near Winter Hill

What are people saying about Puzzling Adventures?

Customer Reviews

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

Molly C.

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 © 4 squirrels

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Puzzling Adventures Highlights

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

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Some of the benefits of time spent outside can include improvements in sleep, blood pressure, cognitive function and physical activity, as well as reduced risks of chronic disease, such as type 2 diabetes, cardiovascular disease and cancer.

Harvard University

https://www.hsph.harvard.edu/news/hsph-in-the-news/spend-time-outdoors-itll-improve-your-health-say-experts/

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

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

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Directory

Amazing Race

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Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

Walking Tour

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

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