Chapter connections I have found thus far:

[dalby2020]

Black Heart Cherry:
Connected to Forty-Eight States via rose (dress and glasses).
Connected to Winter Land via rose (dress and Grateful Dead).
Connected to Granfather's Office via rose / horseracing / Kentucky Derby.

Grandfather's Office:
Connected to Black Heart Cherry as above.
Connected to Full Moon via Hemingway / July 2nd (Hemingway died on July 2nd).
Connected to Egg Hunt via Easter, Hemingway, and Orienteering.

Two Dogs:
Connected to Full Moon (war between brothers)
Connected to Cork (war in general)
Connected to Forty-Eight States via gypsy (wood / dress).

Full Moon:
Connected to Two Dogs as per above.
Connected to Cork as per above.
Connected to Grandfather's Office as per above.

Winter Land:
Connected to Black Heart Cherry as per above.
Connected to Forty-Eight States via rose and rock and roll (Grateful Dead and 'crazy rock-'n-roller').

Cork:
Connected to Two Dogs as per above.
Connected to Full Moon as per above.
Connected to The Bow via reference to iron (iron horse / conquered the iron).

Forty-Eight States:
Connected to Black Heart Cherry as per above.
Connected to Winter Land as per above.
Connected to Two Dogs as per above.

Sand Castle:
I don't have a damn clue about this one!!!

Egg Hunt:
Connected to Grandfather's Office via three links noted above.
Connected to The Bow via firsts.
Possibly connected to Full Moon via Hemingway - July 2nd link.

The Bow:
Connected to Egg Hunt as per above.
Connected to Cork as per above.

[dalby2020]

Collection of "knowns":
Feb 2, 2003
January 1st
Friday, February 22
July 2, '63
April 1923
1945
1956

Diane Smith
Townsand Banks
Gerald Lee Winston

Nantucket
New York
Tri-State Peninsula
Wheat Field
Peach Orchard
Potomac
San Francisco
Appalachia
Southeast Asia
Las Vegas
Boston

Deductions:
Spring, 31 days, Last box of 1st row = Saturday, May 2
Second box of the next line = Monday, May 4

Tri-state peninsula, farmers and waterfowlers = DelMarVa peninsula

July 2 '63, full moon, Wheat Field, Peach Orchard, Mead = 1863 Gettysburg

Friday, February 22, San Francisco, Winter Land, football jersey with 74 = Grateful Dead at Winterland 1974.

Rick, when they stopped it was over, linking Appalachia to Southeadt Asia = Vietnam War.

My sister Ella was two years older, infected by the age 13 = boy is 11.
Went to shore twice each year late spring and early fall, It must remain until we return in the fall = Late spring.
Boston beachgoers = they are from Boston (maybe)

Born on April 1923, birthday celebration tradition, mention of 1945 and 1956 = Easter, April 1.

" Guesses":
Grandfather involved in horseracing and calendar marks first Saturday in May = Kentucky Derby.

Crazy rock-n-roller with multicolored beads strung in his eighteen inch beard and rose-glass shades , rhinestones on his belt and boots = matches description of David Allan Coe.

[Jenny]

I really like the calendar to be May....

What about this? Dark Star won the Kentucky Derby in 1953..... (reason for black star on calendar).... en.wikipedia.org/wiki/Dark_Star_(horse)

And then...

Ernest Hemingway won/was awarded the Pulitzer on Monday, May 4..... for Old Man and the Sea ... (reason for Gold Fish, but also symbol for good fortune)...

We know Duck Miller admired Hemingway, ( eveningsun.newspapers.com/clip/32779127/the-evening-sun/ ) and the book, Hunting and Fishing with Ernie, mentioned in the chapter most likely refers to him.....

Might we have another year nailed down? 1953?

[dalby2020]

Boy - once some of these are out there it seems so clear and you wonder how we missed it. The old hindsight 20/20 thing. Black Star = Dark Star.

I think you did nail 1953 as the year.

[dalby2020]

The problem with these "hunts" is that - once you home in on an idea - you see false connections everywhere.
Lately, I'm tying everything to Grateful Dead and their songs.

Cover: railroad map, Casey Jones.
Introduction - the Hunt: Robert Hunter.
Black Heart Cherry: It must have been the roses; Reuben and Cerise.
Grandfather's Office: Dark Star; Greatest story ever told.
Full Moon: Midnight Moonlight; Ripple.
Winter Land: Saint Stephen; Black Peter.
For the Record: reference to live recordings or studio sessions.
Cork: Soldiers field last Dead show.
Sand Castle: Brokedown palace; Built to last.
Egg Hunt: April 1st shows.
The Bow: Box of Rain , last live song/last chapter.
Bare the cross: Cross Insurance Arena,(April 1, 1985).

It would be interesting if part of the solve involved figuring Grateful Dead song titles and cross referencing those with set lists to narrow down the city. Then specific location is hidden in numbers somehow.

[whispa]

This is so true. I've come up with so many things based on horses and also just animals in general (going with the whistle pig theme) that seem connected or relevant but none of those things seem to help create a solution.
Bare the cross makes me think 4 locations that form a cross when connected so my focus is trying to nail 4 locations near or on the line in the book that might make a cross.

Your connections to Grateful Dead are so good. Dark Star, given all we know about the 1953 Derby and Roses connections etc, is particularly interesting as well as It Must Have Been the Roses and its obvious link to the chapter it's in. Maybe there are only 4 locations/pinpoints necessary that involve the Grateful Dead to hone in on? Maybe 5 if you count the point of intersection of a cross.

[dalby2020]

I agree that is a likely approach.
Clues to locations that, when connected on a map, reveal a location at the intersection.

[dalby2020]

To better explain Grateful Dead connections:

Black Heart Cherry has clues to horse racing and roses. No "direct" clues to Grateful Dead, but recognizable in hindsight with roses and cerise. Main point is that it gets us thinking about horse racing.

Grandfather's Office continues that horseracing thought and leads us to Saturday, May 2nd and the Kentucky Derby. Jenny made the connection between that and the black star on the calendar to get to Dark Star.

Dark star and roses brings us to the Grateful Dead for the first time.

Unfortunately, there are still some middle chapters to figure, but the chapter Winter Land reinforces the importance of Grateful Dead as a clue. It also feeds back to roses as some of the story matches the song "It must have been the roses".

So what can we do with that info?

I think the phrase "align the firsts" and "year of the firsts" means we must figure other firsts (beside first letters of each sentence).

I also think clues can lead us to Robert Hunter - song writer for the Grateful Dead.

"Dark Star" was the FIRST song he wrote after joining the band.
"It must have been the roses" was also written by him and the date referenced in the book, February 22, 1974, was the FIRST time the Greatful Dead performed the song in concert.

I think the purpose of Forty Eight States is to point us toward a song writer.

I don't know if we continue on from there or not. Right now I am looking for more associations between Robert Hunter songs or Grateful Dead "first times" and words or phrases in the book.

Addition:
It appears that Feb 22 was the Grateful Dead's FIRST concert of 1974.

setlists.net is a helpful resource for researching dates and venues.

[Jenny]

Oct 16, 2021 9:07:57 GMT -5 dalby2020 said:

To better explain Grateful Dead connections:

Black Heart Cherry has clues to horse racing and roses. No "direct" clues to Grateful Dead, but recognizable in hindsight with roses and cerise. Main point is that it gets us thinking about horse racing.

Grandfather's Office continues that horseracing thought and leads us to Saturday, May 2nd and the Kentucky Derby. Jenny made the connection between that and the black star on the calendar to get to Dark Star.

Dark star and roses brings us to the Grateful Dead for the first time.

Unfortunately, there are still some middle chapters to figure, but the chapter Winter Land reinforces the importance of Grateful Dead as a clue. It also feeds back to roses as some of the story matches the song "It must have been the roses".

So what can we do with that info?

I think the phrase "align the firsts" and "year of the firsts" means we must figure other firsts (beside first letters of each sentence).

I also think clues can lead us to Robert Hunter - song writer for the Grateful Dead.

"Dark Star" was the FIRST song he wrote after joining the band.
"It must have been the roses" was also written by him and the date referenced in the book, February 22, 1974, was the FIRST time the Greatful Dead performed the song in concert.

I think the purpose of Forty Eight States is to point us toward a song writer.

I don't know if we continue on from there or not. Right now I am looking for more associations between Robert Hunter songs or Grateful Dead "first times" and words or phrases in the book.

Great research, Dalby2020!

[whispa]

Those first few connections seem so solid!

There might be another connection to the Dead - in 1981, Pete Townshend of The Who joined the Grateful Dead on stage in Essen, Germany.. it was their final European tour stop that year. They started in London at the Rainbow Theatre. Townshend of course reminded me of Townsand in the first chapter and Rainbow made me think of the last chapter. If we're talking about the Dead being a main part of this puzzle, 'Townsand/Townshend' seems relevant and if not relevant then what a coincidence!

A note on firsts. The 1953 Derby was also a pretty significant first in the world of horse racing. It was the first time Native Dancer lost a race. When Dark Star won it was a massive upset. So maybe we find two sets of firsts? Might help us narrow down other allusions in the book that we can then link with the Dead's firsts.

[dalby2020]

I read elsewhere of the 53 days in Winterland gives clue to 1953 Derby.
I did not make that obvious connection.

On a separate note:
I finally recognized the allusions in the Bow this evening.

Overall, the book is describing a wild day in the life of Duck Miller.
In short, it's not family-friendly. I might set up a separate site to explain.

But I am getting nowhere in aligning the story with a specific location of a recognizable key.

[dalby2020]

Jerry Garcia died at age 53.

And I've been trying to think which direction we are being pointed with our connections. 
Is winterland somehow a way to point us to the kentucky derby and horseracing?
Or is the kentucky derby and the deduced 1953 leading us to the grateful dead?

I think it's the latter.

Then again, winterland chapter is easily enough to point us to the grateful dead without the other chapter clues.

So I think we are being directed to the songs.
The ones we clearly pick out are 'Dark Star' and 'It must have been the roses' debut.

But Dark Star was not played at the referenced feb 22 1974 winterland concert.

So what is the connection?

I think it must be the songwriter Robert Hunter for the reasons I listed in an earlier post.

Admittedly, I was four states away on the Fenn treasure, half an island away on Fandango, and about a dozen towns away on Trove.
But I got a good feeling about this thought process.

Robert Hunter is leading us somewhere!

Now I am still struggling. I have not yet found further connections.
So Robert Hunter is likely just part of the bigger picture.

Next I am going to set chpts 1, 2, 5, and perhaps 8 aside, clear the slate, put grateful dead out of my mind, and see what other allusions are out there.

I think groups of chapters will lead us to main clues that can then be pieced together into final clues.
Then all the smaller references and allusions will be easily recognizable and lead to a solution.

Although 20 years in, this is solvable.

[dalby2020]

The forth album from the Grateful Dead was Live/Dead.
For The Record = Forth Record?
Align the Firsts - The first track on that Album was Dark Star.

The backing track of the Dark Star single was "Born cross-eyed"
Born / Bare the Cross.