Checkpoint Challenges Customer Photo 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

About Checkpoint Challenges

Do you enjoy hiking or long walks in the park but also want to keep your mind stimulated?

Checkpoint Challenges will take you off the beaten path for an outdoor adventure like no other. Choose your own route between the marked points while perfecting your map reading skills.

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.

Enjoy whenever you want at your own pace...

There is no need to wait for a club meet as our courses are available whenever you are. Enjoyed as either a competitive sport, with rankings for each leg of the course, or a recreational activity, this enriching outdoor pursuit is prefect for any active person or group of adventurers.


Checkpoint Challenges Coolidge Hill

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
Great idea! Can't wait to see more locations added.
James
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer

Checkpoint Challenges Highlights

  • No reservations
  • Running
  • Competition
  • Compass Reading
  • Race
  • Checkpoints
  • Enriching
  • Anytime
  • Outdoors
  • Team building
  • Challenging
  • Physical
  • GPS
  • Active
  • Flat rate price
  • Contest
  • Individuals or groups
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
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Boston Common, 16 Charles St, Boston, MA

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Orienteering Club

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

Navigation Sport

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

Orienteering Event

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

Orienteering Meet

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

Map And Compass Reading

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