Walking Tour near Winter Hill, Massachusetts

Puzzling Adventures are part self-guided walking tour, part interactive game. Uncover hidden secrets of the city while exercising your mind as you explore the city from a completely new perspective.

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.

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

This is a great way to explore and learn about a city!

Stacy H.

This was really fun, it was a nice day and we learned a lot!

Bill S.

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 © Sierras uncles orange shirt

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Puzzling Adventures Highlights

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

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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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directions

73 Tremont St., Boston, MA 02108

More Information

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Directory

Treasure Hunt

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

Walking Tour

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

Scavenger Hunt

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

Amazing Race

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

Escape Room

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

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