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!

Puzzling Adventures

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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 was a great way to spend an afternoon outdoors!

Lynne-Marie A.

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

Rhonda R.

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 © Alyssando

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Puzzling Adventures Highlights

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

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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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Mapping 73 Tremont St., Boston, MA 02108

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73 Tremont St., Boston, MA 02108

More Information

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Directory

Scavenger Hunt

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

Escape Room

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

Walking Tour

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

Treasure Hunt

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

Amazing Race

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

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