I assume the following:
(1) You want to get to Downham Market (DOW) as early as possible.
(2) You have no specific time to return to Bolton (BON) by and just want to return on the same day no matter how late.
(3) You have no railcards.
Target:
Bolton (BON) - Downham Market (DOW)
Anytime Return £99.00
The
Off-Peak Return for this flow is not valid until 0900.
Solution:
Bolton - Doncaster (DON)
Off-Peak Return Route Sheffield £19.80
Valid at any time.
+
Doncaster - Grantham (GRA)
Off-Peak Return £25.40
Valid from 0415.
+
Grantham - Peterborough (PBO)
Anytime Day Return £17.20
+
Peterborough - Downham Market
Anytime Day Return £12.30
This combination allows you to make the following journey:
BON 0430 - 0450 MAN (Manchester Piccadilly) 0544 - 0722 DON 0755 - 0850 PBO 0859 - 0941 ELY (Ely) 0950 - 1006 DOW
This is the earliest you can get into DOW. According to the online journey planner, you cannot arrive earlier than 1006.
The total is
£74.70.
Alternatively if you are prepared to arrive an hour late, then:
Grantham - Ely
Off-Peak Day Return £17.80
Valid from 0900.
+
Ely - Downham Market
Off-Peak Day Return £7.00
Valid from 0900.
This combination means the journey from DON onwards becomes:
DON 0755 - 0829 GRA 0911 - 1013 ELY 1050 - 1106 DOW
The total is therefore
£70.00.
The last journey back is:
DOW 1849 - 1906 ELY 1915 - 1950 PBO 2021 - 2119 DON 2148 - 2221 SHF (Sheffield) 2247 - 0002 MAN 0016 - 0031 BON
It is allowed on both combinations above.
Alternatively for an earlier return journey:
DOW 1707 - 1724 ELY 1752 - 1825 PBO 1839 - 1941 (or 1854 - 1948) DON 1957 - 2020 SHF 2032 - 2132 MAN 2146 - 2206 BON
If you are lucky and get to DON early, you might even catch this:
DON 1942 - 2102 MAN 2120 - 2145 BON
Again both combinations stated above are valid.
Splitting again at Newark Stations saves a few more pence but you won't arrive as early.
I have not checked Advance tickets so there might be cheaper options that way but I doubt that if you want to have a reasonable amount of time in East Anglia, there is a cheaper option out there for flexible tickets. I have checked alternative routeing via Nuneaton, Nottingham, etc and cannot find anything cheaper.
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Virgin and XC don't really do affordable tickets in the morning peak any more.
The 5.05 from Picaddilly to Euston is £30, but it's silly money otherwise.
The only affordable one I can think of relevant to this thread is the Liverpool Stations - Nuneaton (NUN)
Off-Peak Return which comes in at around £36 and is valid from 0415. I tried that one but from NUN onwards I'm stuck with a bunch of SDRs and they total around £80 for the whole jouney or just under £70 if arriving into DOW well past midday, which I doubt is something the OP really wants.