A Perfect Day in Wellfleet
Rail trail to Blue Willow for that egg sandwich on a grilled cinnamon bun, thin chowder at PJ's, oyster happy hour at Winslow's Tavern on Wellfleet Firsts night, and a Moby Dick's frappe to go. Wendy's #1 tip: buy Isabel Sousa Studio ceramics on the spot — they sell fast.
Explore Eastham
with Wendy Taylor | Upfront Clothing & Gifts
From the pages of the 2026 Love Local Field Guide
Start your day at:
Pack up your bike and take a drive to the South Wellfleet rail trail parking lot. From there walk to Blue Willow to try their incredible egg sandwich: egg, cheese, and ham on a grilled cinnamon bun. Heaven!
Spend your morning:
Afterward grab your bike for a ride down Ocean View Drive, stop at various beaches to check out the views, but be sure to swing by White Crest to catch the early to rise surfers.
Grab lunch at:
After trying clam chowder all over the Cape, I have come to realize you either like thick or thin -- I'm team thin, and PJ's Family Restaurant has the best "thin style chowder" that is my absolute favorite.
Spend your afternoon:
While the beaches, ponds and hiking are amazing, if you are visiting on the first Saturday of a summer month and want some fun, don't miss "Wellfleet Firsts." Start with the oyster happy hour at Winslow's Tavern, then go gallery hopping at Farm, AMZehnder, and Jeff Soderberg. You can also enjoy a chocolate and wine tasting at Newcomb Hollow Shop or stop by my shop (Up Front) for a sip and music on the front porch featuring local groups.
Indulge in a treat at:
Moby Dick'sfrappes are so good a friend told me her kids beg for them on a regular basis. I'll take the coffee flavor to go.
End your day at:
Try the tapas and drinks at Scully Joe's, a new eatery right on the bay. A charming old school vibe where the music source is a turn table and LPs. For the perfect sunset, head to Duck Harbor, and make sure to stay for the afterglow, as it's often the best part.
Bonus -- Hidden Gem or Insider Tip:
Down a set of stairs in a light and airy space is the Isabel Sousa Studio. Her handmade ceramics are gorgeous. Don't hesitate on a purchase, grab what you like while there, for her pieces sell fast.
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