Would Tommy have cover on top of the tower?

yes. 3/4 cover +5 AC. due to the battlements. honestly if you duck I would say full-cover but I think our enemies are too ill-equipped already XD

Fiske fires his eldritch blast at the most visibly injured thug  as his imp attacks the bandit capitan engaged with Jetsam

Attack: 16 Damage: 9

imp Attack: 12 Damage: 4

dc 14 con or 15

Hadrian attacks the captain twice.

Attack: 14 Damage: 13

Attack: 18 Damage: 14

Jetsam will stab at his enemy a bunch more times. 

Attack: 10 Damage: 9

Attack: 21 Damage: 5

Attack: 27 Damage: 8

Tommy go shoot shoot with birdies help

Attack1: 26 Damage: 8

Attack2: 24 Damage: 9

The Thug and the captain succumbed to their wounds. Only one captain left and feeling that he just lost all his companions made him bolt and run away. Triggering sentinel from Hadrian and an opportunity attack from Jetsam.

Hadrian:

Attack: 11 Damage: 14

Jetsam to react.

Attack 28, 9 damage. 

With that, the last of the bandit troupe have fallen. 

The old fort would be an ideal place to take a short rest. Will the group rest here?

(we receive 600XP for each of us counting both encounters)

“I could use a sort break to recover my spells at the very least. But if the group chooses to push on I can also do so in my vessel.”

he rummages around to find an adequate seat. 

Tommy hops down and collects his arrows. Short rest sounds great. I could use a snack

“Right.” Jetsam says. “I’m fine to do so.”

Tommy will sit down and eat these guys leftovers. After feeding Birdie he sets her to watch.

Hadrian collected his javelins and took a seat at the campfire. chewed on some jerky before getting a power nap (and rolled a hit die). 

(Once again, don't look if you do not want to be spoilt of the location and threat:)

"ooo were they cooking anything tasty?" Fiske joins by the fire as his spike growth disappears into the ground. Hit Dice Roll: 9

“Let’s see.” Jetsam joined by the fire. Hit die roll:  8

As the team rest their weary selves, they heard scuffling and shrieking from further down the path (which coincidentally is the same way the group should be going). They came upon what seems to be an abandoned camp.

There are ripped up tents everywhere, personal effects scattered all over camp. weapons and armor broken and hewn in places where a fight might have taken place.

But as everyone got to the middle of the camp, about 30 ft around them, the trees seem to converge and the canopy seem to darken where the trees seem to have gone closer to each other.

Hadrian holding his WarAxe (+1) murmured "The trees are watcing us... I feel menace and bloodlust. Get ready for a fight."

(roll for initiative.)

Jetsam grins, pulling his shortsword. 

Initiative: 14

"Oh hells, the trees are acting up too now?! I guess we can always use some spare firewood." Initiative: 4

Why do the treed always lust for blood.

Tommy: 14