Checkpoint Challenges Customer Photo Looking for a local club? No need with Checkpoint Challenges! This innovative new take on orienteering uses your smartphone as both map and compass and allows you to enjoy any of our courses at your own convenience.

Checkpoint Challenges


About Checkpoint Challenges

Are you a fan of hiking or taking long walks in the park but like to keep your mind engaged as well?

Embark on a one-of-a-kind outdoor adventure with Checkpoint Challenges where you will forge your own trail between checkpoints while honing your map reading skills!

Orienteering in the Digital Age...

Much like traditional orienteering, each course consists of a series of points on a map that must be visited in sequence. Participants choose their routes between checkpoints and return to the Start. However, instead of using a large paper map, your smartphone will display only the current map segment with a compass overlay, progress updates, and hints to avoid getting lost.

Your schedule, your tempo...

There's no need to wait for a club meet, as our courses are always available. Whether you enjoy the competitive rankings for each leg or prefer a leisurely recreational activity, this enriching outdoor sport is ideal for active individuals and adventurous groups.

Checkpoint Challenges Everett

What are people saying about Checkpoint Challenges?

Customer Reviews

Great idea! Can't wait to see more locations added.
James
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

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

Navigation Sport

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

Orienteering Club

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

Orienteering Meet

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

Map And Compass Reading

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

Orienteering Event

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