Checkpoint Challenges Customer Photo Forget about fitting a meet into your calendar! This new way to orienteer uses your smartphone for navigation, allowing 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 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.

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 Revere

What are people saying about Checkpoint Challenges?

Customer Reviews

Great idea! Can't wait to see more locations added.
James
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

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

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

Orienteering Event

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

Orienteering Meet

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

Map And Compass Reading

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

Navigation Sport

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

Orienteering Club

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