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!

Unleash your inner detective in Cambridge! Unravel the city's rich history, from its founding in 1630 to its role in the Revolutionary War. Marvel at the world-renowned Harvard University and the Massachusetts Institute of Technology. Uncover secrets of the JFK School of Government and the life of poet Henry Longfellow. A thrilling adventure awaits!

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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.

Explore at your leisure, on your terms...

Because our adventures are self-guided you can play any time on any day - no reservations required. Complete the adventure as quickly as possible to win first place or take your time to enjoy the sights, sounds, smells and tastes of the various locations you will visit.

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Puzzling Adventures near Winter Hill

What are people saying about Puzzling Adventures?

Customer Reviews

I got this as a gift for my wife and we loved it!

Alvin M.

Fun fun fun! great way to experience a new area!

Rhonda R.

We had a great time. Great bonding experience for the whole family.

Angie B.

Image © The Lost Keys

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Puzzling Adventures Highlights

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

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Some studies have shown that natural outdoor environments in urban spaces are more enticing for physical activity and are more likely to motivate people to exercise, leading to higher levels of fitness. Whether it is a park in your neighborhood or exploring the vast landscapes of national forests and grasslands, there are benefits to be had when we step outside.

United States Department of Agriculture

https://www.fs.usda.gov/features/wellness-benefits-great-outdoors

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Rendering Map

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directions

Puzzling Adventures, 65 John F Kennedy St, Cambridge, MA 02138

More Information

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Directory

Amazing Race

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Walking Tour

Chestnut Hill Walking Tour Newton Walking Tour Boston Walking Tour Arlington Heights Walking Tour Glenwood Walking Tour Dorchester North Walking Tour East Cambridge Walking Tour Bay Village Walking Tour Admirals Hill Walking Tour North Brighton Walking Tour Kendall Square Walking Tour Malden Walking Tour Symmes Corner Walking Tour East Somerville Walking Tour Grove Hall Walking Tour Prospect Hill Walking Tour Brighton Walking Tour Beaver Brook Station Walking Tour Roxbury Crossing Walking Tour Waverley Walking Tour Eastview Park Walking Tour West Everett Walking Tour Arlington Walking Tour Beacon Hill Walking Tour Dock Square Walking Tour Wellington Walking Tour Nonantum Walking Tour Cambridgeport Walking Tour Charlestown Walking Tour Brookline Walking Tour Jamaica Plain Walking Tour Clematis Brook Station Walking Tour North Cambridge Walking Tour Allston Walking Tour East Watertown Walking Tour Everett Walking Tour Strawberry Hill Walking Tour Brookline Village Walking Tour Chelsea Walking Tour Medford Hillside Walking Tour Coolidge Hill Walking Tour Edgeworth Walking Tour Spring Hill Walking Tour Belmont Walking Tour Bemis Walking Tour Malden Centre Walking Tour East Boston Walking Tour North Village Walking Tour Inner Belt Walking Tour South Bay Walking Tour Cedar Hill Camp Walking Tour Avon Hill Walking Tour Downtown/financial District Walking Tour Fenway/kenmore Walking Tour Watertown Walking Tour Reservoir Walking Tour Huron Village Walking Tour Mission Hill Walking Tour Mount Auburn Walking Tour Winter Hill Walking Tour Allston Brighton Walking Tour Malden Highlands Walking Tour Ten Hills Walking Tour Chinatown/leather District Walking Tour West Medford Walking Tour Old Cambridge Walking Tour Somerville Walking Tour Sommerville Walking Tour Faneuil Walking Tour Jeffries Point Walking Tour South Boston Walking Tour Newton Center Walking Tour Thompsonville Walking Tour Hendersonville Walking Tour Newtonville Walking Tour Back Bay Walking Tour Va Boston Healthcare System Brockton Campus Walking Tour Longwood Station Walking Tour Beaconsfield Walking Tour Newton Corner Walking Tour Quincy Market Walking Tour Downtown Boston Walking Tour South End Walking Tour East Arlington Walking Tour Wedgemere Walking Tour Glendale Walking Tour Brattle Walking Tour Uphams Corner Walking Tour Aberdeen Walking Tour Oak Grove Walking Tour Medford Walking Tour North End Walking Tour Cambridge Walking Tour West Somerville Walking Tour Waterfront Walking Tour Larchwood Walking Tour West End Walking Tour Coolidge Corner Walking Tour Roxbury Walking Tour Payson Park Walking Tour

Scavenger Hunt

Kendall Square Scavenger Hunt North Brighton Scavenger Hunt Edgeworth Scavenger Hunt Newton Scavenger Hunt Nonantum Scavenger Hunt Glendale Scavenger Hunt Grove Hall Scavenger Hunt Newton Corner Scavenger Hunt Spring Hill Scavenger Hunt Brookline Scavenger Hunt Cambridge Scavenger Hunt Huron Village Scavenger Hunt Newton Center Scavenger Hunt Longwood Station Scavenger Hunt Arlington Heights Scavenger Hunt West Somerville Scavenger Hunt Larchwood Scavenger Hunt Cedar Hill Camp Scavenger Hunt Watertown Scavenger Hunt Mount Auburn Scavenger Hunt Uphams Corner Scavenger Hunt West Medford Scavenger Hunt Faneuil Scavenger Hunt Admirals Hill Scavenger Hunt Strawberry Hill Scavenger Hunt Jamaica Plain Scavenger Hunt East Watertown Scavenger Hunt Waterfront Scavenger Hunt North End Scavenger Hunt Thompsonville Scavenger Hunt Inner Belt Scavenger Hunt Beacon Hill Scavenger Hunt Clematis Brook Station Scavenger Hunt Malden Highlands Scavenger Hunt Va Boston Healthcare System Brockton Campus Scavenger Hunt South Bay Scavenger Hunt Cambridgeport Scavenger Hunt Chelsea Scavenger Hunt Fenway/kenmore Scavenger Hunt Chinatown/leather District Scavenger Hunt Bay Village Scavenger Hunt Payson Park Scavenger Hunt Coolidge Hill Scavenger Hunt Aberdeen Scavenger Hunt Belmont Scavenger Hunt Roxbury Scavenger Hunt Quincy Market Scavenger Hunt Allston Scavenger Hunt East Boston Scavenger Hunt Avon Hill Scavenger Hunt Newtonville Scavenger Hunt Roxbury Crossing Scavenger Hunt North Cambridge Scavenger Hunt Mission Hill Scavenger Hunt Arlington Scavenger Hunt West End Scavenger Hunt Sommerville Scavenger Hunt Eastview Park Scavenger Hunt Dorchester North Scavenger Hunt East Arlington Scavenger Hunt Medford Hillside Scavenger Hunt Winter Hill Scavenger Hunt Chestnut Hill Scavenger Hunt Hendersonville Scavenger Hunt Old Cambridge Scavenger Hunt East Somerville Scavenger Hunt Somerville Scavenger Hunt Boston Scavenger Hunt Dock Square Scavenger Hunt Glenwood Scavenger Hunt Reservoir Scavenger Hunt Malden Scavenger Hunt South End Scavenger Hunt Wedgemere Scavenger Hunt Oak Grove Scavenger Hunt West Everett Scavenger Hunt Malden Centre Scavenger Hunt Brookline Village Scavenger Hunt Everett Scavenger Hunt North Village Scavenger Hunt Allston Brighton Scavenger Hunt South Boston Scavenger Hunt Brattle Scavenger Hunt Downtown/financial District Scavenger Hunt Charlestown Scavenger Hunt East Cambridge Scavenger Hunt Coolidge Corner Scavenger Hunt Prospect Hill Scavenger Hunt Ten Hills Scavenger Hunt Symmes Corner Scavenger Hunt Beaconsfield Scavenger Hunt Beaver Brook Station Scavenger Hunt Jeffries Point Scavenger Hunt Back Bay Scavenger Hunt Bemis Scavenger Hunt Brighton Scavenger Hunt Downtown Boston Scavenger Hunt Medford Scavenger Hunt Wellington Scavenger Hunt Waverley Scavenger Hunt

Escape Room

Bay Village Escape Room Grove Hall Escape Room North Village Escape Room North Cambridge Escape Room Quincy Market Escape Room Medford Escape Room Allston Escape Room Chinatown/leather District Escape Room Brattle Escape Room Watertown Escape Room Chelsea Escape Room Coolidge Hill Escape Room Somerville Escape Room Clematis Brook Station Escape Room Waterfront Escape Room South End Escape Room Jamaica Plain Escape Room Old Cambridge Escape Room Avon Hill Escape Room Downtown Boston Escape Room Cambridgeport Escape Room Spring Hill Escape Room Kendall Square Escape Room Newton Center Escape Room Beaver Brook Station Escape Room Hendersonville Escape Room Payson Park Escape Room Inner Belt Escape Room West Everett Escape Room North Brighton Escape Room Beaconsfield Escape Room Mission Hill Escape Room South Bay Escape Room East Watertown Escape Room Aberdeen Escape Room East Somerville Escape Room Medford Hillside Escape Room Longwood Station Escape Room Edgeworth Escape Room South Boston Escape Room Uphams Corner Escape Room Cambridge Escape Room Charlestown Escape Room Thompsonville Escape Room Oak Grove Escape Room Faneuil Escape Room Everett Escape Room Winter Hill Escape Room Boston Escape Room Huron Village Escape Room East Boston Escape Room East Arlington Escape Room Coolidge Corner Escape Room West Medford Escape Room Malden Centre Escape Room West Somerville Escape Room Belmont Escape Room Mount Auburn Escape Room Glendale Escape Room Ten Hills Escape Room Arlington Heights Escape Room Sommerville Escape Room Jeffries Point Escape Room Prospect Hill Escape Room Strawberry Hill Escape Room Malden Highlands Escape Room East Cambridge Escape Room Glenwood Escape Room Malden Escape Room Eastview Park Escape Room Admirals Hill Escape Room Dorchester North Escape Room Back Bay Escape Room Arlington Escape Room Fenway/kenmore Escape Room Reservoir Escape Room Newton Corner Escape Room Allston Brighton Escape Room Brookline Village Escape Room Cedar Hill Camp Escape Room Wedgemere Escape Room Roxbury Escape Room Downtown/financial District Escape Room Waverley Escape Room Roxbury Crossing Escape Room Dock Square Escape Room Symmes Corner Escape Room West End Escape Room Brookline Escape Room Larchwood Escape Room Beacon Hill Escape Room Va Boston Healthcare System Brockton Campus Escape Room Brighton Escape Room North End Escape Room Bemis Escape Room Wellington Escape Room Chestnut Hill Escape Room Nonantum Escape Room Newtonville Escape Room Newton Escape Room

Treasure Hunt

Watertown Treasure Hunt Fenway/kenmore Treasure Hunt Charlestown Treasure Hunt Thompsonville Treasure Hunt Clematis Brook Station Treasure Hunt Downtown/financial District Treasure Hunt Mission Hill Treasure Hunt Va Boston Healthcare System Brockton Campus Treasure Hunt West Medford Treasure Hunt Oak Grove Treasure Hunt Waterfront Treasure Hunt Malden Centre Treasure Hunt Bemis Treasure Hunt Newton Treasure Hunt West Everett Treasure Hunt Dorchester North Treasure Hunt Hendersonville Treasure Hunt Symmes Corner Treasure Hunt Brighton Treasure Hunt East Arlington Treasure Hunt Arlington Heights Treasure Hunt South Bay Treasure Hunt Roxbury Crossing Treasure Hunt Cedar Hill Camp Treasure Hunt Coolidge Hill Treasure Hunt Chelsea Treasure Hunt Strawberry Hill Treasure Hunt Winter Hill Treasure Hunt Beaconsfield Treasure Hunt North Village Treasure Hunt West End Treasure Hunt Bay Village Treasure Hunt Brookline Treasure Hunt Cambridgeport Treasure Hunt Jeffries Point Treasure Hunt Glendale Treasure Hunt West Somerville Treasure Hunt Downtown Boston Treasure Hunt Belmont Treasure Hunt East Watertown Treasure Hunt Wellington Treasure Hunt Prospect Hill Treasure Hunt Malden Highlands Treasure Hunt South End Treasure Hunt Beacon Hill Treasure Hunt Quincy Market Treasure Hunt Back Bay Treasure Hunt Inner Belt Treasure Hunt Chestnut Hill Treasure Hunt North Brighton Treasure Hunt Longwood Station Treasure Hunt Larchwood Treasure Hunt Jamaica Plain Treasure Hunt Dock Square Treasure Hunt Reservoir Treasure Hunt Newton Corner Treasure Hunt Faneuil Treasure Hunt North Cambridge Treasure Hunt Beaver Brook Station Treasure Hunt Medford Hillside Treasure Hunt East Somerville Treasure Hunt Glenwood Treasure Hunt Wedgemere Treasure Hunt Coolidge Corner Treasure Hunt Mount Auburn Treasure Hunt Arlington Treasure Hunt Edgeworth Treasure Hunt Ten Hills Treasure Hunt Aberdeen Treasure Hunt East Boston Treasure Hunt Everett Treasure Hunt Huron Village Treasure Hunt Brookline Village Treasure Hunt Brattle Treasure Hunt South Boston Treasure Hunt Malden Treasure Hunt Payson Park Treasure Hunt Avon Hill Treasure Hunt East Cambridge Treasure Hunt Allston Brighton Treasure Hunt North End Treasure Hunt Nonantum Treasure Hunt Somerville Treasure Hunt Eastview Park Treasure Hunt Chinatown/leather District Treasure Hunt Boston Treasure Hunt Medford Treasure Hunt Old Cambridge Treasure Hunt Cambridge Treasure Hunt Uphams Corner Treasure Hunt Spring Hill Treasure Hunt Admirals Hill Treasure Hunt Allston Treasure Hunt Newtonville Treasure Hunt Newton Center Treasure Hunt Grove Hall Treasure Hunt Sommerville Treasure Hunt Waverley Treasure Hunt Kendall Square Treasure Hunt Roxbury Treasure Hunt

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