Checkpoint Challenges Customer Photo It's no longer necessary to plan around an event! This modern take on orienteering leverages your smartphone for navigation, enabling you to explore our courses whenever it suits you.

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.

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 Reservoir

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
Did this solo and really enjoyed it. Going to take some friends out next time!
Dave
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

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

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


directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Event

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

Orienteering Club

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

Navigation Sport

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

Map And Compass Reading

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

Orienteering Meet

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