Checkpoint Challenges Customer Photo

Checkpoint Challenges

About Checkpoint Challenges

Are you passionate about hiking or walking in the park but also looking to challenge your mind?

Checkpoint Challenges offers an unmatched outdoor adventure experience. Plot your unique course between checkpoints while working on your map reading skills!

Contemporary Orienteering...

Just like in classic orienteering, each course comprises a sequence of points on a map that must be visited sequentially. Participants determine their own routes between these checkpoints and eventually return to the Start. However, rather than using a full-size paper map, your smartphone will show only the current map segment with a built-in compass, progress tracking, and hints to help you stay on track.

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 Point Shirley

What are people saying about Checkpoint Challenges?

Customer Reviews

This is a must do for anybody who likes hiking, map reading, or orienteering!
Evan
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 2025

Checkpoint Challenges Highlights

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


directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Meet

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

Orienteering Club

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

Navigation Sport

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

Map And Compass Reading

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

Orienteering Event

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