Orienteering Event near Winthrop, Massachusetts

Checkpoint Challenges Customer Photo Don't worry about scheduling conflicts! This modern twist on orienteering turns your smartphone into both map and compass, so you can enjoy our courses whenever you want.

Checkpoint Challenges


About Checkpoint Challenges

Do you enjoy walking in the park or going on hikes but want to keep your mind active at the same time?

Get ready for an outdoor adventure like no other with Checkpoint Challenges. Create your own route between the marked points while refining your map reading abilities!

Orienteering in the modern era...

Similar to traditional orienteering, each course is a series of points marked on a map that must be visited in order. Participants select their own paths between checkpoints, ultimately returning to the Start. However, instead of a large paper map, your phone displays only the current course segment with an integrated compass, progress updates, and hints to keep you from getting lost.

Select your own time and pace...

No need to wait for club meetings as our courses are available whenever you're ready. Engage in competitive action with rankings for each leg or enjoy as a recreational activity. This enriching outdoor pursuit is perfect for any active person or adventurous group.

Checkpoint Challenges Winthrop

What are people saying about Checkpoint Challenges?

Customer Reviews

This was a really cool way to explore the park and it took me places I never would have gone otherwise!
Sophia
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
Always looking for something unusual to do with my girlfriend and this way a hit with both of us!
Noah
Image © Checkpoint Challenges Customer

Checkpoint Challenges Highlights

  • Team building
  • Compass Reading
  • Checkpoints
  • Outdoors
  • Physical
  • Running
  • Enriching
  • Competition
  • Active
  • Race
  • Individuals or groups
  • Flat rate price
  • No reservations
  • Contest
  • GPS
  • Challenging
  • Anytime

After surveying 158 people ages 18 to 87, researchers concluded that orienteering may be more beneficial than physical activity alone. That's because exercising while navigating activates the parts of the brain our ancestors used for hunting and gathering, but which are largely dormant now as people rely on GPS to find their way around.
Time Magazine
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Boston Common, 16 Charles St, Boston, MA

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Map And Compass Reading

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Orienteering Club

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Navigation Sport

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Orienteering Meet

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

Orienteering Event

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