Oak Street is filled with diverse sections. Park near Avery Field near Mitchell.
block 1 – Mitchell Field
block 2 – Avery Field
85 Beech Street at the northeast corner of Avery Field is the former gatekeeper house from the Holyoke Canal System.
Hampden Playground was the original name of Avery Field. It was the first municipal playground in Massachusetts. Nathan Avery the mayor of Holyoke spearheaded the project this get this playground put in place.
block 3 – Oak Street between Dwight and Suffolk Streets
The Dowling Double House at 219-229 Suffolk Street is the oldest structure in this section of the city. It was built in 1889 as a two family home.
block 4 – Oak Street between Suffolk and Appleton Streets
The Roslyn Apartments at 156 Oak was built in 1931. It is one of the few tenement houses on Oak Street.
This block was mostly taken up by Howland’s Hothouses (greenhouses) from 1885 to 1930. They also were located where the Dowling Double House is. Howland’s Hothouses was bought by G H Sinclair and turned into greenhouses.
block 5 – Oak Street between Appleton and Essex Streets
block 6 – Oak Street between Essex and Cabot Streets
211 Oak Street (at the SW corner of Essex and Oak) is the home of Arthur Chapin from 1897 to 1905. From 1905 to 1945 it was the Judd home. William Judd was the president of both Carew Paper and Hampshire Paper both in South Hadley. It is built in the Tudor Revival style.
The George Tyner home at 210 Oak Street was built in 1900. He was the founder of the Holyoke Envelope Company in 1879.
The Louis Strass house at 216 Oak Street was built in 1911.
Second Baptist Church Parsonage is at 235 Oak. It was built in 1899 and was used as their parsonage until past the 1940s.
The Nautilus Building at 245 Cabot is a gorgeous building.
block 7 – Oak Street between Cabot and Hampshire Streets
The Isaac Montague house is at 243 Oak Street.
The Henry Russell house is at 244 Oak.
The Chloe Evans or Maria Outterson house is at 245 Oak.
Amelia Whiting 246
Louise Gallup 247
Albert Magna 248
Lewis Hayward 249
Ettie Richards 250
Alice Hemingway 251
Alice Bennett 252
Ettig Harlow Richards 253
Julia Heywood 254
block 8 – Oak Street between Hampshire and Sargeant Streets
Fairmount Square was at the corner of Oak and Hampshire Streets.
block 9 – Oak Street between Sargeant and Franklin Streets
In the 1910s this last block of Oak was made and developed.