No need to wait for an event that fits your schedule! This innovative new take on orienteering uses your smartphone as both map and compass and allows you to enjoy any of our courses whenever you choose.

Checkpoint Challenges

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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.

Have fun on your schedule and at your speed...

Skip the club meet! our courses are ready whenever you are. Enjoy them competitively, with rankings for each segment, or as a recreational pastime. This enriching outdoor experience is ideal for active people and adventure groups alike.

Checkpoint Challenges South End

What are people saying about Checkpoint Challenges?

Customer Reviews

Great idea! Can't wait to see more locations added.

James

Great idea! Can't wait to see more locations added.

James

Yes, I got lost, but I was soon back on track! I loved the whole experience but especially the helpful warning when I got too far off course :-)

Liam

Image © Checkpoint Challenges Customer

Checkpoint Challenges Highlights

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

Scientists find unusual outdoor activity can help stave off dementia. Researchers studied orienteering, an outdoor sport that exercises mind and body and can also train the brain, helping fight cognitive decline. Now scientists say that the sport - which draws on athleticism, navigational skills and memory - could be useful as an intervention or preventive measure to fight cognitive decline related to dementia.

The Independent

https://www.independent.co.uk/news/dementia-orienteering-outdoor-activity-b2266250.html

Mapping Boston Common, 16 Charles St, Boston, MA

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Boston Common, 16 Charles St, Boston, MA

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Orienteering Meet

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

Orienteering Club

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

Map And Compass Reading

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

Navigation Sport

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

Orienteering Event

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