Walking Tour near Winter Hill, Massachusetts

Immerse yourself in the captivating realm of Puzzling Adventures, where self-guided tours merge seamlessly with interactive puzzles and questions. Reveal the city's secrets while sharpening your mental acuity. Enjoy urban exploration with a twist!

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 © Sierras uncles orange shirt

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Puzzling Adventures Highlights

Team building
No reservations
Photo Challenges
Enriching
Exploration
Informative
Accessible
Outdoor activity
250+ Locations
Kid friendly
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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Mapping 73 Tremont St., Boston, MA 02108

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73 Tremont St., Boston, MA 02108

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Directory

Scavenger Hunt

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

Walking Tour

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

Amazing Race

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

Escape Room

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

Treasure Hunt

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

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