The following timeline provides a chronology of events shown or implied in Spirit Riding Free. Although very few date cues are given in the show, certain events help map the year:
- Holidays and observances such as Christmas, Halloween, harvest celebrations, and birthdays can only come at certain dates annually.
- Weather, and snowfall in particular, is indicative of the season.
- Since a school recess is observed during the summer, scenes in the classroom indicate either that summer has not yet started or that it is over.
- A thirty-day calendar page is shown in "Lucky and the Patchwork Plan", indicating that the events of that episode likely take place in June.
- Circus posters for El Circo Dos Grillos seen in "Lucky and Her New Family Part 1" and "Lucky and the Big Goodbye" give dates.
- The assumption is made that all of the episodes are presented in chronological order, which is evidenced by the sequence progression of various developments and relationships as well as references to the happenings of prior episodes.
Long ago
- The events of Spirit: Stallion of the Cimarron occur.
- Ms. McDonnell finds Thunder.
- At the age of 18, Jim Prescott moves West to the frontier.
- At the age of 16, Milagro Navarro leaves her town of San Jorge with Equuleus, escapes Don Trujillo's henchmen, and joins El Circo Dos Grillos.
- Jim Prescott steals Respero's map, breaks both arms in horse jump, and is nursed by his sister Cora.
- Jim and Milagro marry.
- Jim and Milagro try to find Respero's treasure.
Thirteen years before start of show
- Emma is born in the city.
Twelve years before start of show
- Lucky is born in Miradero.
- Pru is born in Miradero.
- Maricela is born in Miradero.
- Abigail is born in Miradero.
Ten years before start of show
Six years before start of show
- Snips is born on a Saddle Club ride in the wilderness surrounding Miradero.
First spring
- Emma's thirteenth birthday party / Lucky relocates to Miradero / Spirit captured by Mr. Granger's mesteñeros
- Lucky's first day of school / JP & Sons Railroad dynamites Filbert Canyon
- Saddle Club ride
- Jim Prescott takes PALs camping / PALs find Respero's treasure
- Lucky first sees Spirit's herd
- School Bazaar
First summer
- Lucky and Turo free Junipero from Grayson's ranch / Dam bursts, flooding area
- Pru's twelfth birthday / Jim Prescott and Miss Flores first meet
- The PALs put on a "magic show
- Fiesta / Jim and Kate walk together
- Robbers raid frontier banks / Jim and Kate have first date at the café, realize each others' identities
- Church bake-off
First autumn
- Cousin Julian's first stay at the Prescott house / handcar destroyed
- Harvest celebration with communal soup / Turo's Harvest Hunt / Lucky sees Jim and Kate kiss
- Lucky dresses up as a bandit for Halloween, scores three bags of candy
First winter
- Mountain blizzard train delay / Christmas
- Snips swallows the drum major's whistle in the New Year's Eve parade (December 31st)
- Pru and Chica Linda take gold in the Penna Junior Classic horse riding competition (January 2nd)
- Frontier flu outbreak / Miradero blizzard
Second spring
- Tarrell Overland Horse Race in Miradero
- Grayson takes Spirit
- Cannon City Bi-Annual Equine Auction
- Lucky grounded
- Governor born / Governor's Ball
- Grayson buys fishing hole
- PALs rescue Mixtli from Sheriff and Grayson
- Fossil-hunting field trip
- The PALs deputize for the "Mustang Mail
- Earthquake damages Miradero
- PALs discover fool's gold / Cousin Julian's second stay at the Prescott house
- Mountain lion ranges near Miradero, attacks Spirit's herd at Punta Libre / Aunt Cora inducted into Daughters of Miradero Aid Society
- Spirit recovers from mountain lion wounds / Lucky works at Mr. Winthrop's general store
- James Prescott Sr. visits Miradero / Lucky's thirteenth birthday
- O-Mok-See / Aunt Cora leaves Prescott household
- School performs The Whispering Vaquero
- Lucky schemes to keep Aunt Cora from leaving Miradero (May or June)
Second summer
- El Circo Dos Grillos comes to Miradero, gives first performance (June 23)
- Solana injured / El Circo Dos Grillos gives second performance / Jim Prescott and Kate Flores become engaged (June 24)
- Lucky runs away, joins El Circo Dos Grillos
- Pru and Abigail join Lucky in the circus
- Butch LePray robs El Circo Dos Grillos, kidnaps Lucky / Lucky escapes
- PALs' farewell performance with El Circo Dos Grillos (August 19)
- PALs return to Miradero (August 20)
- Maricela debuts bicycle / meteor madness soirée atop Punta Libre
Second autumn
- Mrs. Granger's first aid tutorial
- Mr. Granger's mustang drive to Rancho Conejo
- Halloween, including the PALs' and Turo's Sadie Crouthers pranks in Miner's Grove
- The PALs' overnight trip to the orphanage
- The circus "returns to Miradero / The PALs save it from robbers and give another performance
- Drought / river blocked by landslide / Grayson gouges townspeople for water
- Mr. Granger buys Arabian mares for resale to buyer; they escape and are recaptured
Second winter
- PALs escape dust storm and become Frontier Fillies
- Lucky and Javier kiss on New Year's (January first)
Third spring
- Lucky and Cousin Julian stage a heist for the Scoundrels
- Jim and Kate's wedding / Showdown against Jane / Jim and Kate get married
- Cousin Julian returns to visit the frontier, buys and destroys a hot air balloon
- Kate announces her pregnancy (April 1)
- Lucky learns how to babysit (April 15/16)
- Snow falls in the mountains / the PALs rescue Daisy McWane
Third summer
- The PALs do chores at the Grayson ranch
- The PALs tackle an obstacle course set up for them by Jim and Al to become full-fledged Frontier Fillies
- The PALs invent a "grooming wagon and fix the town clock
- Forest fire at Cedar Gulch outpost / Polly is born
- Dressage competition at Farmbrook Arena
- PALs babysit Polly and Snips Jr. for a day
- The PALs go to the Frontier Fillies Outdoor Summer Jubilee
- Mixtli returns
Third autumn
- Lucky begins eighth grade / Kate takes a maternity leave of absence that turns permanent
- Career day at school
- Lucky's city adventure / interview with Headmaster Madame Gummery
- Miradero or Tides Run; Lucky's decision revealed
- PALs send letters to Palomino Bluffs Riding Academy for enrollment
- The PALs and Maricela meet Mystery
- Eliza Eaton gives Mystery to Maricela
Third winter
- Lucky does chores at Doc Wilkins's, Grayson's and Althea's to earn money for a present
- Lucky and her friends return to the city
- Lucky meets Sally Jessup (Christmas Eve)
- The PALs save passengers on crashed train, and return to Miradero
- Sally Jessup holds her first concert in Miradero (Christmas Day)
Fourth spring
- The PALs go to Palomino Bluffs Riding Academy
Fourth summer
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