Hi Grecofan! My husband and I always stay in Orleans or Eastham, and we really enjoy walking trails from Eastham up to Provincetown. Wellfleet Bay Wildlife Sanctuary is one of our top favorite areas to walk because of the well-kept trails and the great variety of natural areas within the sanctuary. It's the only place with trails where there's an admission fee, but it's well worth the cost. Here's a link where you can learn more about it: massaudubon.org/Nature_Connection/…index.php
Here's a site that has information about a number of trails we especially enjoy: nps.gov/caco/…guide-to-trails.htm Please click on the links under "Virtual Introductions" to get a good idea of the trails. Our favorites are Fort Hill/Red Maple Swamp Trails, Nauset Marsh Trail, Atlantic White Cedar Swamp Trail, Small's Swamp/Pilgrim Spring trails, and Beech Forest Trail.
If you have binoculars, it'd be a good idea to bring them since they're useful to scan the ocean for seals when beach-walking and for seeing beautiful vistas and birds more close-up while walking the trails. Also, before heading off on the beautiful Nauset Marsh Trail, make sure to stop in at the Salt Pond Visitor Center in Eastham to watch short films about the Cape, to walk through the wonderful small museum there (free of charge) and to browse the gift shop (nice bathrooms there, too!) nps.gov/caco/planyourvisit/visitorcenters.htm
In Brewster, just west of Orleans, is the John Wing Trail and the South Trail, as well as The Cape Cod Museum of Natural History-- good for a rainy day activity. Here's their site: www.ccmnh.org/index.php… Also in Brewster is a general store called "The Brewster Store" that's fun for browsing-- full of household goods, gift items, "penny" candy, and a Nickelodeon (costs a quarter nowadays), coffee, baked goods, and a variety of local and national newspapers. http://www.brewsterstore.com/ For another rainy day activity we recently discovered, you might enjoy browsing "Snow's Home & Garden" in Orleans http://www.snowshomeandgarden.com/ for a great variety of household items and gifts.
Our favorite bay-side beaches are in Orleans: Skaket and Rock Harbor. Skaket is best for walking at low tide (for low tide times, check local newspapers or look online for a tide chart) and Rock Harbor is fun to watch charter fishing boats come in when the tide is closer to being high. Both are great for watching sunsets. We also recently discovered First Encounter Beach in Eastham that's lovely and fun to walk at low tide. If the weather and water is too cool when you visit, you can still walk the flats if you have waterproof boots. All National Seashore and Bay beaches are free after Labor Day.
On the way in, after crossing the Sagamore Bridge, please consider stopping in at the beautiful and historic town of Sandwich and walk the Sandwich boardwalk. Here's a Fodor's review of it and it also has directions: fodors.com/world/…review-183870.html Also, if you Google "Sandwich Boardwalk", you'll see many images of it and it shows why it's one of our favorite places to visit while on the Cape.
I hope you have a wonderful time!