Checkpoint Challenges Customer Photo No need to wait for a meet that fits your schedule! This innovative new take on orienteering uses your smartphone as both map and compass and allows you to enjoy any of our courses whenever you choose.

Checkpoint Challenges

About Checkpoint Challenges

Are you a fan of hiking or taking long walks in the park but like to keep your mind engaged as well?

Embark on a one-of-a-kind outdoor adventure with Checkpoint Challenges where you will forge your own trail between checkpoints while honing 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 Point Shirley

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
Always looking for something unusual to do with my girlfriend and this way a hit with both of us!
Noah
Image © Checkpoint Challenges Customer

Checkpoint Challenges Highlights

  • Physical
  • Anytime
  • Individuals or groups
  • Running
  • Checkpoints
  • Race
  • Active
  • Team building
  • Competition
  • Compass Reading
  • Contest
  • Challenging
  • Flat rate price
  • Outdoors
  • No reservations
  • Enriching
  • GPS
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
Mapping Boston Common, 16 Charles St, Boston, MA
directions
Boston Common, 16 Charles St, Boston, MA

Directory

Orienteering Event

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

Orienteering Meet

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

Orienteering Club

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

Map And Compass Reading

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

Navigation Sport

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