.

OP...IMO, people will likely want to get to know you, before they take you into the woods.

If you don't belong to a club, join one. If you're in Mass, you'll need somewhere to practice. Once people at your club know you, you can ask around for advice.

As noted above, more details will get you better answer. If you want to hunt Bambi, you should make that clear, 'cuz it's different from upland birds, or ducks over deeks.
 
Spring turkey is coming or may be here depending on where you live. Turkey are plentiful and relatively easy to call during spring season. There was a time when getting a big Tom was really hard and required hours of dedication. The population has soared and with some minimal scouting and a box call most people can kill a turkey.

Duck is closed until the fall but I suspect you live in a good duck fly way. Barnstable is on the cape I believe, you would have good migratory and sea duck hunting options.
 
OP: You have taken a Hunter Ed course, right? I ask because you say you're new, and you have never shot the gun that you mention planning to use.

It's tough hunting upland birds without a dog. The Wildlife Management Areas are well known, and have plenty of users. Seriously, asking around your Club might give you better feedback than on an online forum.

When you say, "Heirloom Winchester." what are we talking about? A Model 97 Trench Gun, Model 12 Trap, or.....? Not all are good for everything (old doubles would probably be a no-no for steel shot, for waterfowl, for instance.)
 
I’ve taken the course and have been shooting since I was 10 so close to 40 years most disciplines including trap

I have hunted small game, rabbit and squirrel just nothing substantial.

Its an early 70’s Winchester 1400.
You don't allow people to pm you. Send me a pm. Im on cape
 
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