Amazing Race near Winter Hill, Massachusetts

If you love the thrill of the Amazing Race, gather your teammates for an adrenaline-fueled dash across the city, tackling questions and hunting for clues. To claim the coveted top spot on our Puzzling Adventures leaderboard, speed and smarts are your ultimate allies!

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!

Suitable for all ages...

From grandkids to grandparents, our adventures are designed to entertain and engage everyone. With careful consideration for accessibility, almost all of our experiences are wheelchair and stroller friendly. Each adventure is curated to provide a mix of entertainment and enlightenment, ensuring there's something for every member of your group.

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 Winter Hill

What are people saying about Puzzling Adventures?

Customer Reviews

Highly recommend to anyone for a fun day out in the city!

Molly C.

Had a blast! Would definitely do it again!

Candice B.

Our family had a lot of fun on the scavenger hunt!

Lynn C.

Image © Winners Win

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Puzzling Adventures Highlights

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

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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

Amazing Race

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Escape Room

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

Walking Tour

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

Scavenger Hunt

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

Treasure Hunt

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

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