- Berkshire County Courthouse, 76 East Street
- Peace Party House, 76 East Street
- Henry Shaw Briggs
- Berkshire Athenaeum, 44 Bank Row
- Backus, Martin & Wood, 4 – 32 Bank Row
- Easton’s Tavern, 39 South Street
- Martin House, 39 South Street
- Berkshire Museum, 39 South Street
- Campbell House, 39 South Street
- Berkshire Place, Berkshire Home for Aged Women, 89 South Street
- Colt-Pingree House, 101 South Street
- Berkshire Auto Company, 109 South Street
- Colonial Theater, 113 South Street
- West – Sampson – Withington Residences, 157 – 169 South Street
- Butler Block, 120 -124 South Street
- Congregational Church Parsonage, 120 -124 South Street
- Masonic Temple, 116 South Street
- South Congregational Church, 110 South Street
- First Baptist Church, 88 South Street
- The Hotel Wendell, 2-68 South Street (no plaque)
- Berkshire Hotel, 7 North Street
- Berkshire Life Insurance, 7 North Street
- Kennedy Block/Callendar Block, 23 – 35 North Street
- Bush Block, 15 – 23 North St
- Kinnell-Kresge Building, 49 – 59 North Street
- Central Block, 65 – 83 North Street
- England Bros., 89 – 111 North Street
- Burbank Block 141-163
- Persip Park, corner of North Street and Columbus Avenue
- Railroad Depot, corner of North Street and Columbus Avenue
- The New American House, 211 – 229 North Street
- The Burbank Block, Wright Building, 239 – 261 North Street
- Unity Church/Strand Theater, 411 North Street
- Wood Brothers, 417 North Street
- The United States Cantonment, The Berkshire Gymnasium, The Young Ladies Institute, The Second Meeting House, The Maplewood Hotel, 440 North Street
- First Inter-Collegiate Baseball Game in America, 440 North Street
- Academy of Music, 158 – 198 North Street
- Miller Building, 160 – 196 North Street
- Wollison-Shipton Building, 146 – 154 North Street
- Majestic/Palace Theater, 132 – 144 North Street
- YMCA, 132 – 144 North Street
- Rosa England Block, 122 – 130 North Street
- City Savings Bank, 116 North Street
- First Agricultural Bank, 100 North Street
- Dunham Block, 70 -76 North Street
- First Baptist Church, 60 – 74 North Street
- Berkshire Trust Company, 50-54 North Street
- Berkshire Bank, 28 North Street
- West Block, corner of East and North Streets, Park Square
- First Church of Christ, Congregational, 27 East Street
- Bulfinch Church, 27 East Street
- First Meeting House, 27 East Street
- Town Hall/Old City Hall, 43 East Street
- Old Town Hall, 43 East Street
- Original St. Stephen’s Church, 67 East Street
- St. Stephen’s Church, 67 East Street
- Thomas Allen House, corner of East and Allen Streets
- Berkshire Medical Institute Boarding House, corner of East and Allen Streets
- Pittsfield Center, Park Square
- Site of the 1st Agricultural Fair & famous elm tree, Park Square