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.

Entertaining for all age groups...

Whether you're a grade-schooler, a young adult, or a senior, our adventures provide enjoyment for everyone. Almost all of our hand-crafted experiences are accessible to wheelchairs and strollers, prioritizing inclusivity. Each adventure is infused with elements of fun and learning, appealing to a wide range of interests and tastes.

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

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

Molly C.

This was really fun, it was a nice day and we learned a lot!

Bill S.

Our family had a lot of fun on the scavenger hunt!

Lynn C.

Image © Maddie and Andrew

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Puzzling Adventures Highlights

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

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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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directions

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

More Information

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Directory

Treasure Hunt

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

Scavenger Hunt

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

Escape Room

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

Amazing Race

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Walking Tour

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

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