The resplendent beauty within the Bay State is hard to beat, and it’s quite apparent when visiting Cape Cod. With one visit to the Cape, you can easily see why this is the most popular vacation spot in the state. Residents and tourists alike have fallen in love with the beaches, the natural beauty, and the sense of community that is found on this 65-mile-long peninsula.

While towns like Dennis and Hyannis are among the most-visited beach towns on the Cape, Wellfleet is perhaps the most charming and beautiful. Whether you take a day trip to Wellfleet or a weekend trip or longer, you will certainly fall in love with the beaches, the downtown, and everything else it offers. Let’s take a small-town getaway to Wellfleet, Massachusetts.

From the Hawaiian Island of Oahu to the coast of Massachusetts and everywhere in between, come along with OnlyInYourState as we introduce you to the best Small Town Getaways you can take this year. From nature lovers and foodies to history buffs and shopaholics, there’s something for everyone within these unforgettable, two-day itineraries curated by our local travel experts just for you.

Is Wellfleet Worth Visiting?

Do you love the beach? Do you love fresh seafood? Do you love a historic small town with a main street and a great sense of community? If you said yes to any of these, Wellfleet, Massachusetts is absolutely worth visiting.
Melissa Mahoney
Back in 1620, the Pilgrims visited the area that is now known as Wellfleet after first landing in Provincetown. In the 1650s, the first settlement was made here and by the 1700s, fishing became a prominent industry in Wellfleet Harbor. At the time, the area was a part of Eastham and there was an area around the harbor known as Billingsgate with residents who wanted to secede and have it become its own town. In 1763, Wellfleet was finally incorporated as its own town after being part of Eastham.

Over the next centuries, Wellfleet’s economy became routed in fishing, whaling, farming, and commerce. Among its exports, Wellfleet Oysters are the most famous, known worldwide. Today, fresh fish and oysters are still abundant in this small town of less than 4,000 year-round residents.

How To Get To Wellfleet:

The town of Wellfleet is located just over 100 miles from Providence, Rhode Island, and Boston, Massachusetts. Allow between two and 2.5 hours to get here.
Google Maps
From Boston, take Route MA-3 South to the Sagamore Bridge. From there, you’ll travel along US-6 East to Wellfleet. From Providence, take Route 195 East, over the Bourne Bridge to US-6 East. It’s a relatively direct route to get to this charming small town!

Getting Around Wellfleet:

Downtown Wellfleet and the area by Wellfleet Harbor and Mayo Beach are quite walkable. However, despite the walkability factor in town, you’ll definitely need a car to explore the entire town.
Melissa Mahoney
With both bay and ocean beaches, it’s absolutely worth having a vehicle at your disposal in order to explore as much of the town as possible.
Getting around town by bike is another awesome Wellfleet activity. Several miles of the Cape Cod Rail Trail goes through Wellfleet on the ocean side of Route 6. You can then veer off and visit a beach.
Melissa Mahoney
Using a bicycle can get you onto the town beaches for free and no beach sticker is required. But if you decide to go to Marconi Beach, which is part of the Cape Cod National Seashore, you will have to pay an entry fee regardless of whether you drive, bike, or walk.

Best Time To Visit Wellfleet:

While Wellfleet is lovely any time of year, the town really comes to life during the summer months. That’s the time when the population in town increases from roughly 3,500 year-round residents to over 17,000.
Melissa Mahoney
In addition to the increase in population, more restaurants and shops are open, lifeguards oversee the beaches, and there’s a feeling of fun and excitement in the air. Summer is finally here! If you prefer to beat the crowds, visit during late spring and early summer before schools get out or in September after Labor Day.

Where To Stay In Wellfleet:

The town of Wellfleet has plenty of vacation rentals available. From cabins to cottages, campsites, motels, bed and breakfasts, and rental houses, you can have your pick. However, you should try to book your accommodations before the summer begins as they tend to fill up quickly.
Melissa Mahoney
While there is still a chance you can get a last-minute motel room or rental, it’s always best to book ahead of the high season, especially if you plan on visiting in July or August.
If you enjoy camping, try Maurice’s Campground which offers both tent sites and cabins. For motels, there’s the Wellfleet Motor Inn, Even’tide Resort & Cottages, and Endless Coast.
Maurice's Campground/Facebook
If you prefer a house, it’s best to contact one of the local real estate companies that oversee several rental properties around the area.

Morning One: Bike Ride, Coffee & Croissant, and Beach

If you have your own bike, bring it with you to Wellfleet if you can. If not, no worries as there are several bike shops along Route 6 where you can rent one.
Gust/Flickr
Park in the free parking lot at Route 6 and Lecount Hollow Road and here you can start your journey along the Cape Cod Rail Trail, a multi-use trail that covers the original path of the Cape Cod Central Railroad. You will also find the Little Capistrano Bike Shop at this spot. Rent a bike here if you don’t have one.
Head out on your cycling journey. But before or after your ride, stop by PB Boulangerie for coffee and a French pastry. This is a popular spot, especially during the summer months and long lines out the door should be expected. However, it is completely worth the wait.
15 Lecount Hollow Rd, South Wellfleet, MA 02663, USA
Melissa Mahoney
Grab a cappuccino, a latte, or a regular or iced coffee as well as a croissant (our favorite is the almond croissant). This is an authentic French bakery and bistro owned by a chef who came from France. You may actually feel like you’re in Europe instead of a quaint beach town on Cape Cod. PB Boulangerie is open every day except for Tuesdays.
Once you’ve had your fill of coffee and croissants, it’s time to hit the beach! Wellfleet has four town beaches on the ocean side of Route 6. These are Lecount Hollow, White Crest, Cahoon Hollow, and Newcomb Hollow Beaches.
Melissa Mahoney
As mentioned before, if you ride your bike to one of the town's beaches, you can avoid paying for a beach sticker or parking. That is, unless, you visit Marconi Beach which is under the Cape Cod National Seashore. Between morning and evening hours, Marconi charges $25 per vehicle for parking and $15 per person who arrives by foot or bike.

Afternoon One: Downtown Shopping & Exploring and an Upscale Garden Dinner

This afternoon, we will head into town … downtown Wellfleet, that is! While Main Street is on the smaller side, it’s packed with plenty of shops, restaurants, and galleries.
Melissa Mahoney
There are certainly plenty of Wellfleet attractions found downtown.
You’ll even find some small alleyways between buildings that lead to interesting things like Gelato Joy Cafe and some tucked-away studios and stores. You never know what you’ll find around town if you look carefully enough.
Melissa Mahoney
Head downhill off Main Street towards Commercial Street and you’ll have views of the water. Take a stroll across Uncle Tim’s Bridge for water views on both sides.
Melissa Mahoney
If it’s low tide, you can take a walk along the water on the other side of the bridge. Notice all of the fiddler crabs along the sand as you stroll along the picturesque trail.

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From here, you can either head back to your car to drive to Mayo Beach or take an extended walk.
Melissa Mahoney
Once you get to the beach, which has free parking for all (yay!), take a walk on the beach and make your way to the pier. Here, you’ll find Mac’s On the Pier where you can grab fresh seafood and ice cream.
265 Commercial St, Wellfleet, MA 02667, USA
Melissa Mahoney
Across the street from the beach is the Bookstore Cafe with food that’s almost as good as the views. Next to the Bookstore is a park that offers a pavilion and free live music once a week during the summer months, a pretty epic playground, and a skate park. It’s the perfect place to take the kids.
50 Kendrick Ave, Wellfleet, MA 02667, USA
Melissa Mahoney
Once you’ve had your fill of the beach and worked up an appetite, head back to Main Street to Winslow’s Tavern. Set inside a historic mansion built in 1805, you’ll enjoy upscale dining in an atmosphere you can’t find anywhere else in town
316 Main St, Wellfleet, MA 02667, USA
Melissa Mahoney
While you can sit inside the dining room, try to get a table outside in the garden. You’ll love the ambiance of dining on a variety of seasonal dishes here at Winslow’s. And if you're wondering what Wellfleet known for, it's oysters! Do yourself a favor and order some of the world-famous oysters here.

Morning Two: Smoothies and Coastal Hiking

Head to Main Street in Wellfleet and fuel up at BOL before embarking on your morning hike along the coast. BOL offers smoothies, smoothie bowls, avocado toast, gluten-free waffles, coffees, and more.
Melissa Mahoney
317b Main St, Wellfleet, MA 02667, USA
Melissa Mahoney
If you’re health-conscious, this is the place to come. BOL is open seasonally beginning in early summer through part of the fall.
Order your smoothie, bowl, or other breakfast item and either eat outside on a bench along Main Street or find the secret garden next to the Wellfleet Preservation Hall. This circular garden has a fountain and several benches. It’s a serene place to sit and relax as you have your morning meal.
Melissa Mahoney
Once you’re fueled up for the morning, it’s time to hop in the car and head to Great Island. Parking is free here and does not require a permit. A hike here can be as long or short as you’d like and there’s a beach if you feel like laying out or going for a swim.
Melissa Mahoney
Found at Griffin Island and Chequesset Neck Road, Great Island is a peninsula in the Cape Cod National Seashore. Offering hiking trails with water views for most of the way, there’s no other place to hike quite like this on the Cape.
Melissa Mahoney
Head into the woods, and you can find the site of an old tavern. To make this hike more challenging, trek out to Jeremy Point during low tide. You can hike anywhere between 3.9-8.8 miles. Remember to bring your camera because it sure is pretty out here!

Afternoon Two: Kayaking and Dinner With a View

While the beaches are nothing short of spectacular, there are plenty of other things to do in Wellfleet, like kayaking!
Melissa Mahoney
One place you can kayak in is the Wellfleet Harbor where you can launch your vessel at Mayo Beach and paddle over to the marina and then to Uncle Tim’s Bridge. It’s amazing what you can see from the water.
After your kayak, get ready for dinner. We recommend dining at the Bookstore Cafe located across the street from Mayo Beach. Try to get a table outside on one of the decks where you can take in seaside views as you dine.
Bookstore & Restaurant/Google
50 Kendrick Ave, Wellfleet, MA 02667, USA
Rebecca Chickering/Google
The menu at Bookstore Cafe offers a variety of fresh and fried seafood, soups, salads, and desserts. There is also an extensive cocktail, wine, and beer menu. This is a fantastic place to end your day!

 

Not Your Average Bucket List Podcast

Only In Your State’s podcast Not Your Average Bucket List takes a deep dive into Wellfleet, Massachusetts and everything it has to offer. Our hosts, Marisa Roman and Sara Heddleston, discuss what their “Perfect Day” in Wellfleet would consist of. From wildlife hiking trails to sleeping in a cottage by the ocean, take a look at the infographic below to get your own suggestions for the perfect day exploring this small town.

Not Your Average Bucket List

To discover even more about Wellfleet, Massachusetts in a fun, easily-digestible manner, tune in to the episode where we talk all about this charming town. Listen now on Spotify and Apple Podcasts.

 

We hope this Wellfleet travel guide will inspire you for your next day or weekend trip. Are you ready to embark on a small-town getaway to Wellfleet, Massachusetts? How about a weekend trip or longer? There are so many things to do in Wellfleet as well as places to explore and nature and beaches to enjoy. Have you visited this gorgeous small Cape Cod town before? If you have, please tell us all about your favorite things to do here in the comments.

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