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 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

Hunting for a new experience with your kids, teens, family, or your significant other?

Indulge in a Puzzling Adventure, a fusion of self-guided tour, scavenger hunt, and The Amazing Race. Delight in this outdoor escapade, exploring the city in a refreshing way. Follow the route by deciphering clues and tackling challenges to unlock the next phase of your journey. All you need is your mobile device and you're all set for an entertaining new adventure!

Fun for all ages...

Kids, teens, tweens, young adults, seniors, groups, couples, or individuals. Almost all of our adventures are designed to be wheelchair and stroller friendly and all are carefully crafted to be entertaining and informative with something to appeal to everyone.

Flexibility to explore at your own tempo...

Thanks to our self-guided adventures, scheduling is a breeze, no reservations required. Whether you're aiming for the top spot or opting for a more relaxed journey, it's entirely up to you. Take the time to dive deeper into each destination or race to be number one, the choice is yours!

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Puzzling Adventures near Winter Hill

What are people saying about Puzzling Adventures?

Customer Reviews

This scavenger hunt was great for the whole family. We had ages 3 to 63 on our team and we all had a wonderful time!

Karen B.

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 © Los Jefes

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Puzzling Adventures Highlights

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

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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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Rendering Map

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directions

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

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Directory

Walking Tour

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

Amazing Race

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Escape Room

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

Treasure Hunt

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

Scavenger Hunt

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

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