Start: Ireland House, 319 Main St
#1. Bank of New York Building, 238 Main St
#2. Reeve Building, 210-212 Main St
#3. Kramer Building, 206-208 Main St
#4. Whitney Hubbard Gallery, 207-209 Main St
#5. Claudio's, 111 Main St
#6. Preston's, 102 Main St
#8. Greenport Yacht & Shipbuilding, 201 Carpenter St
#9. Jail House, 232 Carpenter St
#10. 151 Bay Ave
#11. 168 Bay Ave
#12. Kendrick House, 152 Bay Ave
#13. Lyons House, 141 Bay Ave
#14. 122 Bay Ave
#15. 123 Central Ave
#16. 145 Central Ave
#17. 163 Central Ave
#18. 320 Carpenter St
#19. 510 Carpenter St
#20. 515 Carpenter St
#21. 608 Carpenter St
#22. Stirling Square, 302-310 Main St
#23. Walter Havens Cottage, 425 Main St
#24. The Times Building, 429 Main St
#25. Phillips House, 433 Main St
#26. Timson Hotel, 437-455 Main St
#27. Greenport Auditorium, 434 Main St
#28. H. E. Wells House, 455 Main St
#29. 500 Main St
#30. Captain Wells House, 530 Main St
#31. Captain Case House, 527 Main St
#32. Grosvenor C. Adams House, 630 Main St
#33. Conklin House, 636 Main St
#34. Civil War Monument, Broad and Main Streets
#35. 162 Stirling St
#36. Townsend Manor Inn
#37. Memorial Park, Main and First Streets
#38. 633 First St
#39. 602 First St
#40. 603 First St
#41. Floyd Memorial Library, 110 North St
#42. 529 First St
#43. Andrew Wiggins House, 519 First St
#44. Whitney Hubbard House, 511 First St
#45. Ackley House, 509 First St
#46. William Corey House, 440 First St
#47. Hartley House, 437 First St