I’ll post my version here. It took me well over an hour to look up what I needed to know. Sometimes I maybe didn’t quite understand the english nuances (or the latin ones). Bugcat’s postmodo iter resumpsi and clivum in oram descendi are both very good. Maybe there are errors in these two, but at first glance, they look very good.
The choice of imperfect and perfect depends on the habituality of the verbal action. The last sentence was kinda hard, as there are in english two main- and one subordinate clause. Greek, for example, has ways to make just one clause with a participle “arriving” and an adjective “a evening-y one”. I usually work more with greek grammar, so I never know exactly what is considered “good style” for latin.
I left town in the morning
Ante lucem ex oppido discessi.
before light-acc-sg-fem out town-abl.sg.ntr depart-1.sg.-Ind-act-perfect
First, I walked down the road, going north
Primum viam ad aquilonem pertinentem inibam.
at-first road-acc.sg.f. to North-acc.sg.m belong-ParticiplePresentActive.acc…sg.f. walk.down-1.sg.Ind.act.imperfect.
A river blocked my path
Flumine iter meum impedibatur
River-abl.-sg-n. path-nom.-sg.-n POSSESSIVE-1.person-sg.-nom.-sg.-n hinder-3.-sg.-Ind.-pass.-imperfect
I paid a toll to cross the bridge
portorium dedi pro pontem transgrediendum
toll-acc.-sg.-n give-1.-sg.-Ind.-act.-perfect for bridge-acc.-sg.-m cross-Gerundivum-acc.-sg.-m (I’m not really sure about my choice of word here)
On the other side, a path led through some fields
trans flumen per campos aliquos ibatur
beyond river-acc.-sg.-n through field-acc.-pl.-m some-acc.-pl.-m go-3.-sg.-Ind.-pass.-imperfect
At noon, I rested under a tree
meridiano sub arbore quievi
midday-abl.-sg.-n under tree-abl.-sg.-f rest.-1.-sg.-Ind.-act.-perfect
A short while later, I resumed my journey
paulo post iterum in viam me dedi
little-abl.sg.n after again in road-acc.-sg.-f REFLEXIVE-1.sg.-acc give-1.-sg.-Ind.-act.-Perfect
I descended a slope, going towards the coast
colle declivi degressi, ora maritima petens
Hill-abl.-sg.-f downward-slanting.-abl.-sg.-f. descend-1.-sg.-Ind.-act.-perfect coast-acc.-pl.-n marine-acc.-pl.-n seek-Participle.Present.active-nom.-sg.-m
My destination was a small harbor town
Oppidulum cum portu petebam.
Little.town-acc.sg.n with harbor-abl.sg.m have.as.destination-1.person.sg.Ind.act.imperfect
It was evening when I arrived, so I spent the night at an inn
advesperascebat cum oppidulum ingrederem, itaque in deversorio pernoctavi.
become.evening-3.sg.Ind.act.imperfect when come.in-1.sg.Subj.act.imperfect little.town-acc.sg.n, so in inn-abl.sg.n. spend.the.night-1.sg.ind.act.perfect.