Jamie S.

Start off your long weekend in Provincetown, the farthest point on Cape Cod. Either catch an early ferry from Boston or arrive the night before and enjoy (though maybe not too, too much) the vibrant nightlife this LGBTQ+-friendly town is known for. Today is your longest day on the bike, so you’ll want

Head north out of Brewster toward Orleans on the CCRT. Just after you cross the townline, you’ll pop off the rail trail onto some scenic side roads in Orleans for a bit of variety as you ride into Eastham, headed toward the Salt Pond Visitor Center. It’s a good spot for toilets, a quick walk through

This route explores the outer and lower Cape, connecting Provincetown, Truro, Wellfleet, Orleans, Brewster, and Chatham on a relaxed loop full of classic Cape Cod scenery. Most of the mileage follows the Cape Cod Rail Trail and paved National Seashore paths, with quiet back roads filling in the gaps

Wake up in Chatham and start your day with a coffee from Snowy Owl or Chatham Cookware. In my opinion, Snowy Owl makes really excellent espresso drinks, but food options are a little lacking. Today’s mileage sits just under 20 miles; it’s purposefully short so you can enjoy Chatham and the surrounding

The Appalachian Trail, or AT, is one of the most iconic long-distance hikes in North America, and is renowned globally among long-distance hikers. The trail stretches over 2,190 miles, giving you the chance to walk from Georgia to Maine. While some aim to complete the full trail in one go (a thru-hike

The Appalachian Trail covers about 160 miles through New Hampshire, and for many, it’s the most dramatic and challenging stretch of the entire AT. From the moment you cross the Connecticut River into Hanover, home to Dartmouth College and one of the friendliest trail towns on the route, the hiking changes

Virginia is the longest section of the Appalachian Trail. Stretching over 500 miles, it clocks in at nearly a quarter of the entire route! It’s sometimes nicknamed the “Virginia Blues” because, while not as rugged as New England or the Smokies, the terrain here demands a steady grind of miles and mental

This first half of the North Carolina–Tennessee stretch of the Appalachian Trail, from the Georgia-North Carolina border to the town of Hot Springs, is where the AT really starts to gain elevation and show off some of the Southern Appalachians’ most dramatic ridgelines. Much of this section hugs the

Maine is the final and often most demanding state on the Appalachian Trail. Running for nearly 280 miles, it’s both the ultimate challenge and the final reward. Trails are rougher, river crossings are frequent, and towns and roads get further apart, making logistics trickier, but the beauty, sense of