Amazing Race near Winter Hill, Massachusetts

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 thrilling journey in Boston! Unravel the city's secrets, from its early European settlers to its modern-day marvels. Answer intriguing questions, snap team selfies, and learn about the city's rich history. Discover the oldest city park in the U.S., explore the subway's electrifying past, and marvel at a 19-ton sculpture. Uncover the city's football roots, its driving laws, and its stunning public garden. You'll even get a taste of Broadway with a Hamilton trivia!

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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!

Perfect for all generations...

Whether you're spending special time with your friends, children, parents, grandchildren, or grandparents, our adventures are tailored to accommodate everyone. Our wheelchair and stroller-friendly experiences are crafted to be both entertaining and informative, appealing to a diverse audience. With activities designed to engage all ages, Puzzling Adventures goal is to provide a memorable experience for everybody who participates.

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

This was so fun!

Bob A.

This was a great experience!

Natalie M.

We had so much fun we can't wait to try another adventure. Such a fun family activity and a great way to see the city.

Sandi K.

Image © A and J Rockin It

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Puzzling Adventures Highlights

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

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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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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

Walking Tour

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

Scavenger Hunt

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

Treasure Hunt

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

Amazing Race

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

Escape Room

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

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