Amazing Race near Winthrop Highlands, Massachusetts

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Are you a fan of the Amazing Race? Grab some teammates and dash around the city while deciphering questions and searching for answers. You will need to be the quickest and the smartest to win top spot on our Puzzling Adventures leaderboard!

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

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

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.

Play on your own schedule at your own pace...

Since 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 speed.

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Puzzling Adventures near Winthrop Highlands

What are people saying about Puzzling Adventures?

Customer Reviews

Great experience for the whole family!

Alan B.

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

Rhonda R.

I liked how each clue showed us little known facts about the city. It made finding local eateries and sights easy. Very fun!

Taylor V.

Image © Miller Clan

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Puzzling Adventures Highlights

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

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Spending time outdoors can improve overall health and wellness. The outdoors offers many opportunities to be physically active. Time outdoors may also promote mental health and stress reduction.

Centers for Disease Control and Prevention

https://www.cdc.gov/cancer/skin/basic_info/outdoors.htm

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directions

Boston Self-Guided Scavenger Hunt, 73 Tremont St., Boston, MA 02108

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Directory

Walking Tour

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

Escape Room

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

Scavenger Hunt

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

Treasure Hunt

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

Amazing Race

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