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!

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.

You choose the time and the pace...

Our courses are available whenever you are, eliminating the need to wait for a club event. Participate competitively, with rankings for each leg of the course, or enjoy as a recreational activity. This enriching outdoor pursuit is perfect for any active person or group of adventurers.


Checkpoint Challenges Brookline

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
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

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

Aerobic exercise releases chemicals in the brain that foster the growth of new brain cells. And when you use a map and connect it to landmarks, you stimulate growth between brain cells.
Harvard University Medical School
Loading map...
directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Club

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

Navigation Sport

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

Orienteering Meet

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

Map And Compass Reading

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

Orienteering Event

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