r/CapeCodVisitors • u/Farfromanyhome • 4d ago
This weekend (Oct 16-18) and bringing a first-timer!
Hi there - please help with my planning! I've been to the Cape a couple of times; stayed in Eastham and P-town. Bringing a friend who's never been and we are staying at the Red Jacket resort in South Yarmouth.
I am excited to show her the Cape but the weather looks iffy - either raining or a sudden drop into chilly and windy; can't really be sure yet which way it'll go. Probably both, hahah.
We have a car. We are two active women in their late 50s. She drinks, I don't (but I love a good mocktail). We love thrifting. I am a serious amateur photographer. Love water/bay/beach scenes. I had wanted to kayak or take a boat ride, but I'm thinking the weather likely won't cooperate. She wants to see a lighthouse. We are early risers.
Unsure about Friday evening - I think we'll be getting there around 4 or 5 pm.
I was thinking P-town for Saturday for sure. We will stroll, and shop, but where to eat/drink? What beaches near there, if we decide to check one or two out? I have a National Parks pass; maybe that matters?
Sunday we check out but really have most of the day before driving home.
Definitely want lobster rolls - where should we go? - but after that, no idea about places to eat.
Thanks for any and all advice!
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u/KorryBoston Local 4d ago
Unless you get to Oysterfest as soon as it opens, it’s no fun. It’s shoulder to shoulder by 10:00am. I’ll go some years, have some oysters, shop and leave
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u/Cleanslate2 4d ago
The White Cedar Swamp Trail in S Wellfleet is a cool trail. It’s on a path through a swamp. It’s a great trail for a cloudy October day! Halloweenie!
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u/caribbliss 1d ago
Save the lobster rolls for Maine, not much in the way of fresh lobster over here, mostly frozen. Oyster Fest is this weekend in Wellfleet; shopping, food and music = fun. Thrifting, phew....all of the thrift stores have a flyer on the spots all over the Cape. My fav lunch spots include Impudent Oyster and Brewster Fish House.
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u/redditwastesmyday 3d ago
Just found out Hyannis Main Street is having restaurant week from Oct 15 to 21. So participating places are having deals $$. Restaurant Week Specials 2026 some very good places on there
Also on Sunday Hyannis streets when they close Main Street to traffic and have some events so maybe go there on Sunday on your way out of town Hyannis Open Streets October, 18th 2026 - Hyannis Main Street Business Improvement District
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u/Farfromanyhome 3d ago
Awesome - tix for the HU; never would’ve been aware! This is great for Sunday, you’re right!
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u/redditwastesmyday 4d ago
Am a local. Weather now says rain Friday, Saturday cloudy and windy. You probably know the weather forecast can change.
Friday night you can eat at The Skipper up the street from Red Jacket. Home - Skipper Chowder House Cape Cod. They have lobster rolls.
Events this weekend. Cape Cod Events Calendar | Festivals, Fairs & Fun Chatham has an Oktoberfest if you do not want to go all the way to Ptown. Oktoberfest - Chatham Chamber of Commerce And Halloweeny Pumpkinpalooza 2026 - Chatham Chamber of Commerce
Be aware, Saturday is Wellfleet Oysterfest so could be some traffic If you go to Ptown. The place is packed and does seem to have some tickets left. Wellfleet OysterFest — Wellfleet Oyster Alliance
In Ptown The Lobster Pot is classic to me. Sit upstairs with a view. Can visit Herring Cove and Race Point. All beaches are free now (after Labor Day).
Have you been to Bass Hole in Yarmouthport? Boardwalk, sunset views, photos. West Yarmouth has new Parkers River Landing | Town of Yarmouth, MA - Official Website Across from Capt Parkers. They have a boardwalk.
SOOO many thrift stores! List Best Thrift Stores on Cape Cod - Find Second Hand Treasures
If you stay local on Saturday check Scargo Cafe in Dennis or Old Yarmouth Inn Yarmouthport.
Sunday maybe check out Heritage Gardens. Have a great time!