Experience everything this iconic destination is famous for from sandy beaches and lighthouses to seafood shacks and coastal bike paths. We'll explore like locals and dine in style throughout this can't-miss Weekend Getaway.
Friday, August 2nd
3pm at Eldredge Park
77 Eldredge Park Way, Orleans, MA 02653
The Weekend Getaway (limit 30 participants) will meet in Orleans for a leisurely 20-mile cruise to shake out the travel and kick off our weekend. This ride will take us to two bayside beaches - one in Orleans and another in Brewster - before looping back to Hog Island Beer Co. in Orleans to toast the weekend!
Saturday, August 3rd
9:30am at Cape Cod National Seashore Salt Pond Visitor Center
50 Nauset Rd, Eastham, MA 02642
This best-of ride will take us to: First Encounter Beach in Eastham on the bayside (where the Mayflower landed and first encountered Native Americans in 1620); the iconic dunes of White Crest Beach in Wellfleet; Wellfleet Harbor for lunch, where we can watch fishing boats unload their catch while kite surfers play in the waves; and, the Coast Guard Station in Eastham. Our ride will end coasting over the boardwalk pictured at the top of the page.
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Dinner on the Waterfront
6:00pm at Sesuit Harbor Cafe
357 Sesuit Neck Rd, Dennis, MA 02638
We will reconvene for dinner in Dennis at the waterfront Sesuit Harbor Cafe. This seafood shack has the best lobster rolls on the Cape plus a perfect view of the sun setting over Cape Cod Bay as the boats come and go from the harbor. We’ll be dining outside so bring your favorite sweater or wind breaker.
Sunday, August 4th
9:30am at Chatham Town Parking Lot
30 Bearses Byway, Chatham, MA 02633
To cap off the weekend, we’ll meet at the “elbow” of the Cape in Chatham at . This 20-mile day will include views of sandy beaches, the Chatham Lighthouse, saltwater-weathered cottages, waterfront estates, and more. This ride is as scenic as it is rewarding, ending for lunch at that Chatham Fish Pier. We’ll enjoy lunch with a show: your choice of fresh-caught options enjoyed from the viewing deck while the seals beg fisherman for scraps as the boats unload their haul.
Tyler Wren
Farm to Fork Fitness Adventures founder (and former professional cyclist!) Tyler Wren will be with you for every turn of the pedals throughout the weekend. As your lead guide, he’ll share his knowledge of the region while fostering a rewarding group riding dynamic.
SELF GUIDED ADVENTURE
Can’t make it to the big event?
Get season-long access to our best routes . Our curated itinerary takes the effort out of planning so you can focus on the adventure! Explore fantastic rural roads, meet local artisans, and enjoy farm-sourced food all along the way. Learn more here.