Amazing Race near Winter Hill, Massachusetts

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Inspired by the excitement of the Amazing Race, rally your team for a high-speed pursuit through the city streets, decoding questions and hunting down clues. Only the quickest and sharpest minds will triumph and secure their place atop 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

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!

Enjoyed by people of all ages...

From children to seniors, from groups to individuals, our adventures cater to all ages and preferences. Nearly all our experiences are meticulously designed and accommodate wheelchairs and strollers, ensuring inclusivity for all. Each adventure is thoughtfully curated to blend entertainment and education, with something to captivate every participant.

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.

Very enjoyable!

Kelly L.

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 © HAYNESFAM

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Puzzling Adventures Highlights

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

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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

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Directory

Walking Tour

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

Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

Amazing Race

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