Navigation Sport near Brookline Village, Massachusetts

Checkpoint Challenges Customer Photo In the spirit of orienteering, this activity pairs exercise with navigation, providing an engaging and competitive experience for active individuals of all abilities and fitness levels.

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 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.

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 Brookline Village

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
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
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

  • Compass Reading
  • Race
  • GPS
  • Active
  • Flat rate price
  • Team building
  • Contest
  • Physical
  • Challenging
  • Competition
  • Individuals or groups
  • Outdoors
  • Checkpoints
  • Running
  • Enriching
  • Anytime
  • No reservations
This sport teaches self-reliance and terrain discovery to the point where it could save lives. Orienteers acquire the skills and techniques to relocate themselves and to continue on to their destination, no matter what.
Health Fitness Revolution

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Boston Common, 16 Charles St, Boston, MA

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Navigation Sport

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Orienteering Event

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

Map And Compass Reading

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

Orienteering Meet

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

Orienteering Club

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