Checkpoint Challenges Customer Photo No more scheduling conflicts! This revolutionary orienteering experience uses your smartphone as both map and compass, giving you the freedom to enjoy our courses whenever you choose.

Checkpoint Challenges

About Checkpoint Challenges

Do you like taking walks in the park or hiking but wish you could engage your mind too?

Set off on an extraordinary outdoor adventure with Checkpoint Challenges. Improve your map reading expertise as you navigate your own path between checkpoints!

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 Coolidge Corner

What are people saying about Checkpoint Challenges?

Customer Reviews

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

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

Mapping Boston Common, 16 Charles St, Boston, MA

directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Event

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

Map And Compass Reading

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

Navigation Sport

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

Orienteering Meet

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

Orienteering Club

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