Checkpoint Challenges Customer Photo This modern version of orienteering is an outdoor challenge that mixes physical exercise with navigation, offering a competitive experience for participants of any skill and fitness level.

Checkpoint Challenges

About Checkpoint Challenges

Do you enjoy hiking or long walks in the park but also want to keep your mind stimulated?

Checkpoint Challenges will take you off the beaten path for an outdoor adventure like no other. Choose your own route between the marked points while perfecting 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.

Have fun on your schedule and at your speed...

Skip the club meet! our courses are ready whenever you are. Enjoy them competitively, with rankings for each segment, or as a recreational pastime. This enriching outdoor experience is ideal for active people and adventure groups alike.


Checkpoint Challenges West End

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
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

  • Active
  • Physical
  • Anytime
  • GPS
  • Individuals or groups
  • Competition
  • Race
  • Running
  • Checkpoints
  • Outdoors
  • Challenging
  • Enriching
  • Flat rate price
  • No reservations
  • Compass Reading
  • Contest
  • Team building
Instructors have discovered that orienteering identifies with each scholastic order, from math to history to ecological attention to public approach, and it does as such in new and intriguing manners.
Core Spirit Human & Planetary Enhancement

directions
Boston Common, 16 Charles St, Boston, MA

Directory

Navigation Sport

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

Orienteering Meet

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

Map And Compass Reading

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

Orienteering Event

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

Orienteering Club

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