Of the 262 mss pages, 147 pages are diary entries, the rest memorandum and accounts. The two diary volumes (v. 7 & v. 8) contain sailing trips on the St. Lawrence River taken in the summers between 1892-1895, and a three month trip taken in 1893 to Florida, stopping at various places along the way.  The memorandum and account books include Hill and his wife's accounts with Jefferson County National Bank and Merchant's Bank, and accounts for wages paid for laborers on his farm, monies spent for foodstuffs for his family, material for maintenance of the farm, and the day to day miscellaneous items for the household and farm. There also appears to be an inventory inscribed for "E. Boynton's goods," she was Hill's second wife Elizabeth. These goods appear to have been sold and recorded.

Orrin D. Hill was the son of Calvin P. Hill (1801-1880) and Lois Waite (1801-1873). He was born in Watertown, Jefferson County, New York, in the year 1827. Orrin's grandfather, Asa Hill (1770-1856), was a Holleston, Massachusetts pioneer to Oneida County, New York. The Hill family originally started out in Rodman, New York, sometime between 1805 and 1807 and after Orrin's father married in 1824, they removed to Watertown when Orrin's father purchased his brother Lorenzo Dow Hill's farm.

In 1852, Orrin married Martha M. Boynton and settled on a farm in the area. Martha died in 1884 and Orrin married again in 1886 to Emma A. Boynton, his first wife's sister. Hill was the assessor for the town for four years and afterwards elected to be Rodman's town supervisor twice for 1873 and 1874. In his early life he was a school teacher.

Thousand Island Park, a place where Hill appears to have kept a summer home and his sailboat, was located 20 miles north of Watertown. It sits on the St. Lawrence River, bordering Canada. East Rodman, where Hill relocated later in life was located about 10 miles south of Watertown.

Orrin D. Hill died at age 80 on May 26th, 1908, at his home in East Rodman. He is buried at Brookside Cemetery, at Watertown.  Hill was very active in the Methodist Church, particularly the Rodman charge and northern New York. He filled every office of his church and for many years was a very successful superintendent of the Sunday school. He spent many summer seasons at Thousand Island Park where he had a summer home. He was well known at Thousand Island as "Captain Hill," who delighted so many with his sailboat, often taking his friends for a sail on the St. Lawrence River.

Hill's diary for sailing on the St. Lawrence provides an interesting picture of life on the river and the pleasure and leisure of a late 19th Century family, and those who lived or summered in the Thousand Islands, or the nearby areas. Hill notes people and places he visited, various landmarks along the river, sailboat races he attended, and the various aspects of sailing the St. Lawrence in the 1890s. Some examples of the entries for this diary are as follows:

1892

"June 16^th,

Suffered mental depression with grip the night before. Started out for a trip with Em, Alice, Carrie, Lee and Miss Buckingham. Tacked across the river and then again and sailed to Grindstone opposite Clayton. Wind very fresh down the river. Stood across to the head of Round Island, went down South side. Stood to Cliff House, reefed and went in to dock P & S. Afternoon went out along with 3 reefed mainsails. Came back and made moorings."

"August 20^th,

Sailed around Well's Island with Mrs. Russell and Short. Misses Carrie, Lee and Russell, Em, Alice and Clark. Wind up river puffy. Started double reefed. Shook reef out of mainsail and after reading the Bay shook reef out of jib. Fine sea below the bay. Capt. Noor was a head of me. We stopped at Darlings dock for our lunch. Wind kept dying away. Noor tried to catch me and pass but the Reindeer was too fleet of fast. We had a fine party and nice trip but was very tired and nervous at night."

"August 25^th,

Went to Clayton in the Nightingale to see the races. Wind strong N. East. Fine race, 3 boats capsized. One went over 3 times and the boys righted her and went on. Had a terrible rain last night. 6 or 8 inches water fall."

"September 3^rd,

Sailed over to Fisher's Landing with Em and Alice to visit Capt. Robbin's folks. Staid to dinner. Sailed over with the Capt and his mail bags, took over L. D. White with us. Sailed home at 4 o'clock. Day very nice. At 4 o'clock day very nice indeed, wind fresh down the river. Dead calm, no sailing up to September 8^th."

"September 9^th,

In afternoon started out with Em and Alice and Mrs. Patterson and Sweet. Very light breeze from Northward. Sailed around Hemlock Island, took about 3 hours. Most of the time not a ripple on the water and yet had steerage way all the time. Sailed through "The Cut", never sailed through ___in the world. The trip was a phenomenon in that there was no breeze, was aloft and did not touch the water. The old ladies had a great time. Better then I did."

1893

"June 24^th,

Started at 11 A.M. for a sail with Em, Alice and Minnie Buckingham. Sailed to foot of Long Island and on the way home saw the Spanish fleet of Caravils  on its way to World's Fair. Fair wind up the river and a strong wind down to come home. Had a delightful sail day, warm and clear."

"July 19^th,

Sailed around this island and in to Lake of the Isles with Alice and Nell, Mr. and Mrs. Davis and Misses Buckingham and Griffith. Had a nice cool day and strong wind, north wind in A.M. Landed at Westminster and at the bay and at Dewolf's in the Lake of the Isles on the Canada side. Took our lunch there. Started out in morning with 2 reefed mainsail and jib. Shook out one at the bay and got on all sail at Westminster. Wind light from there home. Got in at sundown. Had a nice party and nice day out. Got very tired. Can't help it."

"July 28^th,

Started for Clayton with Em and the girls and Horace Wait in forenoon. Had a fine run up and back. In afternoon took the girls, Em and Miss Buckingham up to Bluff Island for a bath. Came to anchor and carried them ashore in the dingy. Fell and hurt my hip badly in the boat. Wind died down all away before we reached moorings."

"August 5^th,

Started out with Alice, Lew and Will. Sailed down to Fine View to see the Indian Camp. Fell off the horn into the river, got wet all over head and ears. Some way unknown to me. Got lame in my knee. Carried out in P.M. Mr. and Mrs. Freeman, Mr. and Mrs. Brown, Miss Ferris, Em and Alice. Beat up the river with S.W. wind to near Cumming's Point. Sailed home behind Round Island. Had a nice party and a nice trip. The Reindeer out sailed the Watson boat and also a strange yacht. Done them up in good style. My knee got very stiff and lame."

1894

"August 3^rd,

Took out for a short sail. Bert Norr and Frank Moore. Took two reefs in mainsail and full jib. Had too much sail. Then blew hard down river. Came on to blow a gale in the afternoon. I went up to Clayton on Nightingale. While there the Reindeer parted cable and went ashore at Mrs. Lee's and seawall and would have gone to pieces but for Mr. Quackenbush and son and John Perry, Frank Moore and many others! Thank God."

"August 28^th,

Started out about 11 and with my folks and Mr. and Mrs. Reed and Mr. and Mrs. and Miss Kay for a trip around Grindstone. Wind light. Ran on to a shoal in Canada waters between two islands. Had a great time getting off. Reed and I got into the river and pried her off. The Frazer kindly tried to pull us off but failed but took off our crowd. Ran into Leak Island Bay and reefed. Ran on to Hickory Island and lunched. Wind fresh N.E. Got home at sunset, thankful."

1895

"June 26^th,

Started out at 8 A.M. for a trip up the river with Em and Alice. Had the wind S.E. up as far as Round Island. Fell dead calm for 2 hours. Came up from the South and had a nice run up to Brown's Point Light. Ran under the Point and close reefed. Had a rough run across the gap with a heavy chop sea. Wet us down nicely. After we passed Center Brother's Light it got squally, too much so to reach into the bay so made Stella harbor with some difficulty. Found an excellent harbor and made up our camp for the night. Day clear in A.M. but threatening rain in P.M."

"June 27^th,

Had a thunder shower in the night but our shelter was complete and we were too tired to be disturbed. We explored the town in the morning and started out about 10 A.M. Found a nice breeze down the channel and dead ahead but it was a perfect day for sailing. Clear and fine. Had a dead beat of it up Adolphus Reach to the Stone Mills then got a shot that sent us up to the mouth of Ray Bay flying. Found a poor place to land but hauled up at "Goose Point" and landed and made camp and staid over night safely near Mr. Mallory's house. They were very cordial to us. The shores from Kinston up and along Amherst were very fine."

His trip to Florida is contained in the second diary for 1893, Hill traveled by rail and boat to Florida, stopping at the cities of Baltimore (MD), Washington, DC, Richmond (VA), Charleston (SC), and Savannah (GA). Once he reaches Florida he visits many cities and towns: Deland, Interlachen, Jacksonville, Orlando, Palatka, Rockledge, St. Augustine, Silver Spring, and Titusville. The diary starts on January 16th and he arrives in Florida by February 3rd. While at these cities and towns, he takes day trips to outlying areas, all fully described, where he visited, the buildings, vegetation and who he meets. The diary ends on March 6th.

Hill moves through the north fairly quickly, reaching Baltimore:

"January 20^th,

We left Rochester at 6:35 A.M. Went past the fine farms of that section until we reached Canandaigua, though the vineyards of the west shore of Seneca Lake and the beautiful blue open water of the lake to Watkins and down through the valleys and low mountains of Pennsylvania and along the beautiful Susquehanna to Williamsport and Harrisburg and so on to Baltimore. The day began with snow and cold but cleared up fine and it was a delightful ride. Only the car was badly ventilated and the hot foul air gave me the headache but we found a quiet home and room at the Albion but with strange faces and customs about us. We got in about 7 P.M."

"January 21^st,

After breakfast at the Albion we took a coupe and went up to Mrs. Parker's and found that Lib and Annie had been down to the station waiting for us. Fannie and I went down to look for them and missed them again. We found them nicely provided for and they met and treated us with great hospitality. In the P.M. we rode about the city on Jed's car and saw the crowd at the market place. Found the young ladies and gentlemen fine looking and nicely dressed with nice brick buildings. Baltimore is a fine busy city of 500,000, Jed says. Met more politeness in the street cars than North."

In Washington, DC, Hill caught a glimpse of President Harrison and visited the White House, amongst other sites:

"January 28^th,

Started out before breakfast for 409 G. St. Did not find Mr. Brown. Afterwards Em and I went by cable car to Georgetown to see Willie Maher. Found him alright. Came back and walked around the White House and grounds. Got a glimpse of President Harrison. In the P.M. visited the Capitol, looked over the elegant paintings. Went up into the dome. Saw the Potomac River for a long distance above and below the city. Sat down to rest in the President's room. The most elegant room I ever saw. Visited the House of Representatives. Saw them in session. Visited the Senate Chambers. Saw but a few of the Senators, &c&c. Got home very tired and spent a fine evening in chat with the "girls". Day was misty and chilly but did not freeze."

While in Charleston South Carolina he also made a day trip over to Sullivan's Island and explored a cemetery and other sites:

"February 3^rd,

In Charleston found the acquaintance of Mr. George F. Scott of Ashville N.C. who was with us at Sullivan's Island. A very pleasant man whom I hope to meet again. Went out to the Bonaventure Cemetery with Em and Mr. Lawshe of N.J. Was completely captivated with its beauty of a kind I had never seen in the North. We also went over to Thunderbolt, an oyster depot and summer resort on the Delta of the Savannah River. Day bright and hot as a day in July North. Made the acquaintance of Mr. Rich of N.C., and ex-confederate soldier who went with us to Forsyth Park and around the city to the wharves. Stood under the fine monuments to the dead confederates and shook hands as brothers of the same glorious country."

Once in Florida Hill visits St. Augustine:

"February 9th,

Started for St. Augustine about 11:30, reached there place to dinner, & then Em & I started out to see the sight. We were located at The Abbey House kept by Mrs. Abbe on the cor of St. George & Fort Sts visited to old city gates Fort Marion & its dungeons the sea wall, crossed the ferry to Anastasin Isld & to the store of the shore of the ocean at South beach & saw the [oput] breakers roll in on the sands. Shwery & warm got very tired but had a very interesting day, one of the best we had since Savannah.

"February 10^th,

Em and I visited the hotels Alcusar, Cordova and the Ponce De Leon, the three grandest hotels in the US if not in the world. Took a carriage and rode around the city and to Dr. Converse's orange grove. In the P.M. left by train by the porters mistake so we took another trip to Sound Beach. Start in morning to return to Palatka. Day clear and very hot, 80 degrees in shade. In evening Em and I started for a walk. City not very well lighted but is the nicest place seen by us in Florida yet."

Hill seems quite happy to leave his accomodations at St. Augustine:

"February 7^th,

Left the Glenada House with its nasty niggers to eat their own stuff. With great pleasure took the steamer Eliza Hancox for a trip up the St. John's to Palatka. Had an elegant trip on the wide smooth waters of the St. John's. The river is 4 or 5 miles wide. Shores low with woods and very monotonous. Very interesting and restful day hot as a June day North. Left at 9 o'clock and reached Palatka about 2 P.M. found rooms with Mrs. Dr. Eaton and board with Mrs. Houghton."

 

Hill uses Palatka, Florida as a base, taking several day trips. His firs visit is to Silver Spring where he:

"February 14^th,

Took a barge with the other passengers and floated over the clear water of the Springs to see the great cavities where this wonderful subterranean river comes to the surface. Walked about over the dead city of Silver Springs. Started down the river at noon and saw again the wonderful river. Saw several alligators. Arrived at Palatka about 3 o'clock in the morning of the 15^th. Went up to our room, washed up and changed clothes and tried to rest out day. Hot and clear with breeze from S. West. Received a letter from Alice and wrote home a reply."

He also takes a short train trip to Interlachen Florida, where he spent the day and had dinner with the hotel owner. The following day he leaves Palatka for Deland, finding all of these towns populated with northerners and takes a room, spending several days there. Being a farmer, he writes about the various orange groves and other vegetation and foodstuffs that he sees.

By the third week of February, Hill starts for Rockledge (FL), where visits the park, the groves, the town, and enjoys it. He then takes a train for Titusville (FL), where on the train he encounters a boy with a dog:

"February 22^nd,

Started at 8:30 from Rockledge for Titusville by the Steamer St. Augustine. Cold strong north wind. Had a very stormy tedious passage. Caught cold and chills. Stopt at several landings for oranges by the carload. 3 hours to go 25 miles! Took train for Sanford, reached there in time and went to Sirrene House. E and I walked about this old blighted city. Day cold but sunshine. Had a boy and dog on train. Boy had a pug nose and dog was a pug dog. This is a true sketch made by the Indians while in state of confinement."

Hill then proceeds to draw a portrait of the boy and his dog in his diary. Hill and his wife then move on to Orland, where they take in the fair, describing what they see. After Orlando, they begin their return trip by going to Palatka, spending a couple of days, then taking a boat up the St. John's River to Jacksonville (FL), where they board a steamer and travel to Charleston (SC), then New York City, arriving on March 6th, the last entry in the diary. Throughout Hill's diary he keeps track of the money he spends for train and steamer tickets, hotels, dinners, and other essentials and miscellaneous purchases. The Florida portion of this diary is documented in 30 of the 52 pages and is excellent for the late 19th Century views of the "northern" (early tourist) towns in Florida that he visits.