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!

Next Generation Orienteering

Like conventional orienteering, each course includes a sequence of map points that must be visited in order. Participants select their own routes between checkpoints, eventually returning to the Start. Instead of a full-size paper map, though, your phone will show only the current course segment, complete with an integrated compass, progress details, and hints to keep you oriented.

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 Downtown Financial District

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
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

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

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

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

Orienteering Event

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

Orienteering Meet

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

Orienteering Club

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

Map And Compass Reading

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