The daughter of Louis[1] and Anne Wolfrom, Anna was born about 1872 in Massachusetts and was raised in Kansas City, Missouri.

[13] In 1917, Wolfrom taught at Northeast High School in Kansas City and lived in the Estes Park cabin a few months a year.

[14] In December 1903, while studying at Oxford University in England, Wolfrom was visited by an acquaintance, Guy Robert LaCoste, who negotiated acquisition of land in Estes Park.

[15] Wolfrom and LaCoste then met with Windham Wyndham-Quin, 4th Earl of Dunraven and Mount-Earl, Estes Park's largest land owner.

[6] She did most of the work herself, bringing lumber, supplies, and groceries in a wheelbarrow along a steep path from Estes Park, which was about 5 miles (8.0 km) away.

[6][14] Hikers passed her home when the Wind River Trail[6][7] was opened along Aspen Brook.

[6][17] Her initial customers arrived on the trail after she had a road built, doing most of the work herself,[14] people also drove to the Wigwam Tea Room.

[14] By 1921, she lived in Estes Park nine months of the year and spent the rest of the time traveling and buying merchandise for the Wigwam Tea Room.

[4] After her death, her Estes Park property was owned by the Coburn and Reichardt families.