- Trip 1 - 10 places 3.4 miles in Category:Maryland
- Link to the Trip Map
- St._Frances_Academy_(Baltimore,_Maryland) - Private_schools - 39°18′08″N 76°36′30″W / 39.3022°N 76.6083°W
- The_Ivy_Hotel - Buildings_and_structures - 39°18′13″N 76°36′46″W / 39.3035°N 76.6129°W
- Frederick_and_Pennsylvania_Line_Railroad_Museum - Museums - 39°18′08″N 76°37′01″W / 39.3022°N 76.6169°W
- Center_Stage_(theater) - Theatres - 39°17′53″N 76°36′45″W / 39.2981°N 76.6125°W
- Old_Town,_Baltimore - Neighborhoods - 39°17′41″N 76°36′25″W / 39.2947°N 76.607°W
- Maryland_Art_Place - Art_galleries - 39°17′22″N 76°36′26″W / 39.2895°N 76.6071°W
- University_of_Maryland_Biotechnology_Institute - Universities_and_colleges - 39°17′11″N 76°36′21″W / 39.2864°N 76.6058°W
- Jonestown,_Baltimore - Historic_Jewish_communities - 39°17′18″N 76°36′04″W / 39.2883°N 76.6011°W
- National_Academy_Foundation_School - Magnet_schools - 39°17′47″N 76°35′51″W / 39.2964°N 76.5975°W
- Johnston_Square,_Baltimore - None - 39°18′11″N 76°36′21″W / 39.3031°N 76.6057°W
- Trip 2 - 10 places 4.6 miles in Category:Maryland
- Link to the Trip Map
- Joint_Global_Change_Research_Institute - None - 38°58′17″N 76°55′20″W / 38.9713°N 76.9221°W
- The_Art_Gallery_at_the_University_of_Maryland - Contemporary_art_galleries - 38°59′07″N 76°56′51″W / 38.9853°N 76.9475°W
- Tawes_Theatre - University_and_college_theatres - 38°59′09″N 76°56′55″W / 38.9859°N 76.9485°W
- Ludwig_Field - College_lacrosse_venues - 38°59′17″N 76°57′02″W / 38.9881°N 76.9506°W
- University_of_Maryland_School_of_Music - Music_schools - 38°59′26″N 76°57′02″W / 38.9906°N 76.9506°W
- University_of_Maryland_College_of_Agriculture_and_Natural_Resources - Agricultural_universities_and_colleges - 38°59′30″N 76°56′27″W / 38.9917°N 76.9408°W
- University_of_Maryland_College_of_Information_Studies - American_Library_Association_accredited_library_schools - 38°59′18″N 76°56′29″W / 38.9882°N 76.9415°W
- Robert_H._Smith_School_of_Business - Business_schools - 38°59′15″N 76°56′24″W / 38.9875°N 76.94°W
- Herbert_Wells_Ice_Arena - Indoor_arenas - 38°58′34″N 76°55′23″W / 38.9761°N 76.9231°W
- Center_for_Advanced_Study_of_Language - National_Security_Agency - 38°58′26″N 76°55′32″W / 38.974°N 76.9256°W
- Trip 3 - 10 places 13.3 miles in Category:Maryland
- Link to the Trip Map
- Jennings_House - Government_buildings - 38°58′52″N 76°29′09″W / 38.9811°N 76.4859°W
- Ogle_Hall - Houses - 38°58′43″N 76°29′05″W / 38.9786°N 76.4847°W
- Triton_Light - Lighthouses - 38°58′54″N 76°28′36″W / 38.9817°N 76.4767°W
- McMullen_Hockey_Arena - Indoor_ice_hockey_venues - 38°59′37″N 76°27′33″W / 38.9936°N 76.4592°W
- Severn_River_Bridge - Road_bridges - 39°00′23″N 76°30′13″W / 39.0064°N 76.5035°W
- Annapolis_Area_Christian_School - Schools - 38°59′47″N 76°31′58″W / 38.9964°N 76.5328°W
- Westfield_Annapolis - Buildings_and_structures - 38°59′23″N 76°32′42″W / 38.9897°N 76.5451°W
- Annapolis_High_School_(Maryland) - International_Baccalaureate_schools - 38°58′27″N 76°33′53″W / 38.9742°N 76.5647°W
- Maryland_Hall_for_the_Creative_Arts - Music_venues - 38°58′26″N 76°30′20″W / 38.9739°N 76.5056°W
- Terwilliger_Brothers_Field_at_Max_Bishop_Stadium - Sports_venues - 38°59′11″N 76°29′43″W / 38.9864°N 76.4954°W
- Trip 4 - 10 places 25.4 miles in Category:Maryland
- Link to the Trip Map
- Red_House_Tavern - Houses - 39°19′49″N 77°01′03″W / 39.3303°N 77.0174°W
- Woodmont_Academy - Private_schools - 39°20′47″N 77°00′25″W / 39.3464°N 77.0069°W
- Piney_Run_Park - Nature_centers - 39°23′53″N 76°59′10″W / 39.3981°N 76.9862°W
- Eldersburg,_Maryland - Census-designated_places - 39°24′03″N 76°57′05″W / 39.4008°N 76.9514°W
- Pfefferkorn_House_and_Granary - Plantation_houses - 39°17′41″N 76°59′20″W / 39.2948°N 76.989°W
- Isaacville,_Maryland - None - 39°15′09″N 76°59′33″W / 39.2525°N 76.9925°W
- Longwood_(Glenwood,_Maryland) - Plantations - 39°16′00″N 77°03′00″W / 39.2667°N 77.05°W
- Keewaydin_Farm - Buildings_and_structures - 39°16′00″N 77°03′00″W / 39.2667°N 77.05°W
- Glenwood_Middle_School - Public_schools - 39°17′51″N 77°01′27″W / 39.2975°N 77.0243°W
- Cooksville,_Maryland - Unincorporated_communities - 39°19′12″N 77°01′14″W / 39.32°N 77.0206°W
- Trip 5 - 10 places 21.6 miles in Category:Maryland
- Link to the Trip Map
- Harford_Day_School - Private_schools - 39°32′58″N 76°20′48″W / 39.5494°N 76.3467°W
- The_John_Carroll_School - Roman_Catholic_secondary_schools - 39°32′20″N 76°19′59″W / 39.5389°N 76.3331°W
- Stoney_Demonstration_Forest - Protected_areas - 39°30′50″N 76°15′00″W / 39.5139°N 76.25°W
- Riverside,_Harford_County,_Maryland - Populated_coastal_places - 39°28′35″N 76°14′42″W / 39.4764°N 76.245°W
- Winters_Run - Rivers_and_streams - 39°26′21″N 76°18′27″W / 39.4393°N 76.3075°W
- Constant_Friendship,_Maryland - Unincorporated_communities - 39°28′13″N 76°18′39″W / 39.4703°N 76.3108°W
- New_Covenant_Christian_School - Christian_schools - 39°29′22″N 76°18′50″W / 39.4894°N 76.3139°W
- Bel_Air_South,_Maryland - Census-designated_places - 39°30′10″N 76°19′08″W / 39.5028°N 76.3189°W
- Patterson_Mill_Middle_and_High_School - Public_middle_schools - 39°30′26″N 76°19′27″W / 39.5073°N 76.3243°W
- Ma_and_Pa_Trail - Hiking_trails - 39°32′02″N 76°21′50″W / 39.5339°N 76.3639°W
- Trip 6 - 10 places 21.4 miles in Category:Maryland
- Link to the Trip Map
- Bishop_Walsh_School - Private_elementary_schools - 39°39′40″N 78°47′27″W / 39.6611°N 78.7908°W
- Caiuctucuc - Populated_places - 39°39′00″N 78°46′01″W / 39.65°N 78.767°W
- Thomas_B._Finan_Center - Psychiatric_hospitals - 39°39′24″N 78°44′09″W / 39.6567°N 78.7358°W
- Tri-State_Zoological_Park - Buildings_and_structures - 39°39′49″N 78°42′54″W / 39.6636°N 78.7149°W
- Nicholas_Mountain - Mountains - 39°37′36″N 78°42′32″W / 39.6267°N 78.7089°W
- Allegany_County_Fairgrounds - Fairgrounds - 39°36′31″N 78°47′54″W / 39.6086°N 78.7983°W
- Amcelle,_Maryland - Unincorporated_communities - 39°36′28″N 78°48′55″W / 39.6078°N 78.8153°W
- Bowling_Green,_Maryland - Census-designated_places - 39°37′28″N 78°48′20″W / 39.6244°N 78.8056°W
- Haystack_Mountain_(Maryland) - Ridges - 39°37′48″N 78°49′14″W / 39.6301°N 78.8206°W
- Brush_Tunnel - Railroad_tunnels - 39°41′24″N 78°48′50″W / 39.69°N 78.8139°W
- Trip 7 - 10 places 12.2 miles in Category:Maryland
- Link to the Trip Map
- St._Maria_Goretti_High_School - Schools - 39°39′50″N 77°42′11″W / 39.6639°N 77.7031°W
- University_System_of_Maryland_at_Hagerstown - Universities_and_colleges - 39°38′33″N 77°43′16″W / 39.6425°N 77.7211°W
- Barbara_Ingram_School_for_the_Arts - Performing_arts - 39°38′30″N 77°43′14″W / 39.6417°N 77.7206°W
- Funkstown,_Maryland - Towns - 39°36′33″N 77°42′27″W / 39.6092°N 77.7075°W
- Antietam_Academy - Buildings_and_structures - 39°37′12″N 77°43′48″W / 39.6199°N 77.7299°W
- South_Hagerstown_High_School - Public_schools - 39°37′14″N 77°43′57″W / 39.6206°N 77.7325°W
- Hagerstown_Roundhouse_Museum - Railroad_roundhouses - 39°38′39″N 77°43′59″W / 39.6442°N 77.7331°W
- Discovery_Station - Transportation_museums - 39°38′35″N 77°43′22″W / 39.6431°N 77.7228°W
- North_Hagerstown_High_School - International_Baccalaureate_schools - 39°39′45″N 77°42′59″W / 39.6625°N 77.7164°W
- Fountainhead-Orchard_Hills,_Maryland - Census-designated_places - 39°40′59″N 77°42′59″W / 39.6831°N 77.7164°W
- Trip 8 - 10 places 20.2 miles in Category:Maryland
- Link to the Trip Map
- Laboring_Sons_Memorial_Grounds - Monuments_and_memorials - 39°25′15″N 77°24′26″W / 39.4207°N 77.4071°W
- Weinberg_Center - Performing_arts_centers - 39°24′50″N 77°24′42″W / 39.414°N 77.4117°W
- Frederick_station - Railway_stations - 39°24′43″N 77°24′20″W / 39.4119°N 77.4055°W
- Linganore,_Maryland - Census-designated_places - 39°25′02″N 77°18′39″W / 39.4172°N 77.3108°W
- Balmoral,_Maryland - Unincorporated_communities - 39°25′15″N 77°18′02″W / 39.4208°N 77.3006°W
- Linganore_AVA - American_Viticultural_Areas - 39°25′59″N 77°16′01″W / 39.433°N 77.267°W
- Tuscarora_Creek_(Monocacy_River) - Tributaries - 39°27′31″N 77°22′26″W / 39.4587°N 77.3739°W
- Monocacy_River_bridge_and_viaduct - Viaducts - 39°27′54″N 77°23′33″W / 39.465°N 77.3925°W
- Tuscarora_Creek_(Monocacy_River)_bridge - Railroad_bridges - 39°27′48″N 77°23′37″W / 39.4633°N 77.3936°W
- Clover_Hill,_Maryland - Former_census-designated_places - 39°27′25″N 77°25′38″W / 39.4569°N 77.4272°W
- Trip 9 - 10 places 22.7 miles in Category:Maryland
- Link to the Trip Map
- Worcester_Preparatory_School - Private_elementary_schools - 38°18′58″N 75°13′18″W / 38.3162°N 75.2216°W
- Rackliffe_House_(Assateague_State_Park) - Reportedly_haunted_locations - 38°19′01″N 75°13′01″W / 38.317°N 75.217°W
- Sinepuxent,_Maryland - Former_populated_places - 38°18′47″N 75°09′07″W / 38.3131°N 75.1519°W
- Roland_E._Powell_Convention_Center - Convention_centers - 38°22′05″N 75°04′26″W / 38.3681°N 75.074°W
- Isle_of_Wight_Wildlife_Management_Area - Protected_areas - 38°23′35″N 75°06′26″W / 38.3931°N 75.1072°W
- St._Martin_River - Rivers_and_streams - 38°24′10″N 75°08′30″W / 38.4028°N 75.1417°W
- Sherwood_Forest,_Worcester_County,_Maryland - Unincorporated_communities - 38°22′03″N 75°09′02″W / 38.3675°N 75.1506°W
- Glen_Riddle_Farm - Horse_farms - 38°21′N 75°09′W / 38.35°N 75.15°W
- Ocean_Downs - Buildings_and_structures - 38°21′09″N 75°09′50″W / 38.3524°N 75.1639°W
- Calvin_B._Taylor_House - Biographical_museums - 38°19′38″N 75°13′13″W / 38.3272°N 75.2204°W
- Trip 10 - 10 places 27.1 miles in Category:Maryland
- Link to the Trip Map
- St._Michaels_Middle/High_School - Public_middle_schools - 38°46′48″N 76°12′57″W / 38.7799°N 76.2159°W
- The_Crab_Claw_Restaurant - Seafood_restaurants - 38°47′16″N 76°13′14″W / 38.7878°N 76.2206°W
- Doncaster,_Talbot_County,_Maryland - Unincorporated_communities - 38°47′03″N 76°07′54″W / 38.7842°N 76.1317°W
- Glebe_Creek - Rivers_and_streams - 38°47′40″N 76°06′30″W / 38.7944°N 76.1083°W
- Avalon_Theatre - Buildings_and_structures - 38°46′27″N 76°04′30″W / 38.7742°N 76.075°W
- Trinity_Cathedral_(Easton,_Maryland) - Episcopal_cathedrals - 38°46′34″N 76°04′14″W / 38.7762°N 76.0706°W
- Seth_Demonstration_Forest - Protected_areas - 38°45′05″N 76°02′10″W / 38.7514°N 76.0361°W
- Easton_High_School - Schools - 38°45′21″N 76°03′57″W / 38.7558°N 76.0658°W
- Town_Creek_(Tred_Avon_River) - Landforms - 38°41′37″N 76°10′01″W / 38.6937°N 76.1669°W
- Bellevue,_Maryland - Populated_coastal_places - 38°42′12″N 76°11′04″W / 38.7033°N 76.1844°W