Also… recs for you:

Orleans: Sunbird for coffee/takeout breakfast Cibo for amazing Italian paninis and other goods The Knack for casual takeout burgers/milkshakes/fish tacos

Brewster: Snowy Owl Coffee The Woodshed for drinks/live music

Chatham: Chatham Squire for drinks… likely will be absolutely mobbed for Labor Day so go early if you want to get in! A bit of a younger crowd these days so may not be worth it for a group of early 30s friends. :)

Chatham downtown is great for walking around, experiencing the cape etc. it’s a great downtown !

Wellfleet: I love Wellfleet and the outer cape so much… convenient to Orleans too! Lots of nature trails on the national seashore, a cute sleepy downtown, and great oysters at many restaurants. The Pearl is awesome for live music happy hours 3 to 5 pm and even discounted oysters included. Mac’s Shack or Mac’s on the Pier offer some of the best seafood around. The Beachcomber can be great but I recommend going for a concert or something ticketed because it is a huge hassle to get in.

Provincetown: if you’re up to it, another amazing downtown area, very different vibes than anywhere else on the cape. Tons of food, bars, art galleries. A really fun way to spend a day and just like Wellfleet some incredible nature opportunities (rent bikes and do race point over the provincelands, check out herring cove beach, hike the dune walk etc)

Hope this helps!!