Checkpoint Challenges Customer Photo Don't worry about scheduling conflicts! This modern twist on orienteering turns your smartphone into both map and compass, so you can enjoy our courses whenever you want.

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.

Select your own time and pace...

No need to wait for club meetings as our courses are available whenever you're ready. Engage in competitive action with rankings for each leg or enjoy as a recreational activity. This enriching outdoor pursuit is perfect for any active person or adventurous group.


Checkpoint Challenges Cambridgeport

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
Great idea! Can't wait to see more locations added.
James
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

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

Orienteering can be a great way to reduce stress and improve your mental health. Being in nature and navigating through unfamiliar terrain can be calming and grounding. It can also help to improve your problem-solving skills, focus, and spatial awareness.
Dove Med

Rendering Map

directions
Boston Common, 16 Charles St, Boston, MA

Directory

Navigation Sport

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

Map And Compass Reading

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

Orienteering Event

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

Orienteering Club

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

Orienteering Meet

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