The Best Cape Cod Road Trip Itinerary

Cape Cod Rotary aerial view

Chatham is a great base for your trip to Cape Cod, and there is so much to do on the Cape that it can keep you busy for days!  With drives along the coast, day trips to the islands, and tours of all sorts to fill your time, here are our recommendations for your visit to this beautiful area.

The beauty of the Outer-Cape, a road trip to Provincetown – Cape Cod National Seashore, Eastham, Wellfleet & Truro 

One of the most popular driving trips that we recommend to our guests is to take a day to go to Provincetown up at the tip of the Cape. Located approximately 35 miles from Chatham and less than an hour drive, this destination is a must!  There are loads of things to see on the way, so don’t worry about being stuck in your car all day.  Heading north out of Chatham in the morning, we suggest that your first stop is Eastham at the Salt Pond Visitors Center.  Here you can learn about the formation of the Cape, watch a film, visit the museum or shop.  You can also walk around the Nauset Marsh Trail or the Buttonbush Trail and view some of the beautiful landscapes.  Down the road from the Visitors Center, you will find Coast Guard and Nauset Light beaches.  Coast Guard Beach is consistently rated in the top 10 most popular beaches in the U.S.  If you decide not to stop at the beach, drive up and have a look at Nauset Light which is just a short drive along the shore from Coast Guard Beach and have a look – it is famously seen on the Cape Cod Potato Chip bags.

After you leave the Visitors Center, keep on heading North.  If you are feeling peckish, we highly recommend that you stop at PB Boulangerie and Bistro in Wellfleet.  Here you can choose some of their fantastic French pastries to bring along with you – if they make it out of the shop.  They also have a full menu of sandwiches, salads, and other delicious entrees if you want something a bit more substantial.  If you are a fan of food, kitchen gadgets, bulk spices and teas, jellies and jams, and all sorts of other goodies that are great for presents, the Atlantic Spice Company is just the ticket.  Just down the way from the Spice Company is Truro Vineyards.  They have some amazing wines – as well as gins and rums – and they offer frequent tastings so you can try some of the vintage that you can purchase and take home.  There are often food trucks there as well, so you can enjoy a leisurely lunch on their spacious grounds.

Once you make it to Provincetown, there is a plethora of things to do!  Whale watching tours with Dolphin Fleet are opening beginning July 6 (check the website for reservations as capacity will be reduced); ride in the dunes with Art’s Dune Tours, or cruise Commercial Street’s many artisan shops and restaurants. To get your daily steps in, you can climb the Pilgrim Monument; visit Race Point Lighthouse, walk along the beach and perhaps spy a whale from shore… the options are endless.  Whatever way you fill the day, you are sure to have a fantastic time.

The beauty of the Upper-Cape, a road trip to Sandwich 

Another great day trip is to Sandwich, the Cape’s oldest town. Just a short 30 minutes’ drive from the Inn.  Start off your morning with a stroll down the boardwalk at Town Neck Beach.  The boardwalk crosses marshes and streams and is full of wildlife to watch as you walk along planks inscribed with the names of donors who contributed to rebuilding the walkway after a storm destroyed most of it.  Relax a while among the sand dunes at the beach before you head back into town and off to the Heritage Museum and Gardens.  These vast gardens have acres and acres to roam among brilliant flowers and trees.  There is always something in bloom, and there are all sorts of art displays to see as well.  There is an art gallery, a carousel to ride, a special exhibition gallery, a museum of classical cars, and a tea shop for a refreshing treat.  Take your time through here, you will have a great time! (Be sure to check their website to see which exhibits are currently open).

For lunch, head to the Dunbar House Restaurant and Tea Room.  They have a huge selection of delicious teas to try, as well as different goodies on their menu.  You can have a traditional tea of finger sandwiches and assorted desserts, or try some of their sandwich options like the Ploughman’s Lunch or a Curried Chicken Salad.  Across the street from the Tea House is Dexter’s Grist Mill, which is a fully functioning mill where you can purchase some of their fresh ground cornmeal.  This is also a beautiful place for photos, so you will see lots of people posing for a memorable shot.  Head over to the Sandwich Glass Museum to view some beautiful works of art.  There are live glass blowing demonstrations as well, so you can see the fascinating process of how they made the beautiful creations exhibited around you.  As you walk through the museum, you will get a look at the long and involved history of glass, and see how the craft has changed over the years.  Be sure to spend some time in the gift shop to find that memorable piece to take home.  Take your time on the drive back to the Inn along route 6A.  This quiet road takes you past historic homes and past sweet little shops that you can stop in if you feel like stretching your legs.

The beauty of the islands, Martha’s Vineyard and Nantucket 

Martha’s Vineyard, famous for its high-profile celebrity and presidents vacationing there, is more laid back and hip than  “its neighbor” Nantucket.  From the Inn, the ride to Falmouth and the passenger ferry is about a little over 1 hour and will only cost you $8.50 each way and a nominal fee for parking at the satellite parking sites. Once on the island, you can rent bikes, take a school bus island tour, or use public transportation to hop from town to town. The bike trail connecting Oak Bluffs and Edgartown goes along the ocean and features some spectacular views. If you are more adventurous head to the highest point of the island for a picture-perfect view of the famous Aquinnah Light. Grab a lobster roll and enjoy the views. When you are back in Oak Bluffs make sure you take a self-guided tour of the colorful gingerbread village, hop on the oldest carousel in the U.S., and try a scoop of Mad Martha’s Ice Cream.

Nantucket is a very popular spot with our guests.  This fabulous little island is a great spot to spend a day.  Take your breakfast to go and catch the Freedom Cruise Line Ferry out of Harwich Port, a short ten minutes’ drive from the Inn. For more flexibility and a chance to get a glimpse of the Kennedy’s Compound drive to Hyannis and take one of the ferries Steamship Authority or Hy-Line.  The ride is about an hour and a half, so sit back and relax.  Once you dock, make your way along the cobbled streets into the historic heart of the village.  We suggest you book one of Gail’s Tours if you want to see more of the island than you would on foot.  She does a fabulous job pointing out all of the local spots and will regale you with fun facts and stories about the island.  The Whaling Museum is also a very interesting spot to visit.  The museum is a goodly size, so be prepared to spend some time here.  It will show you the history of the island and give you a good education on the history of whaling which was the lifeblood of the island for a very long time.  Make sure you make it to the roof and take in the incredible view of the harbor and town. 

For a fun afternoon, head out to Cisco Brewery.  They have a free shuttle from the center of town, and the brewery has something for everyone.  Not only do they have great beer, but they also have wines and cocktails with their own liquor.  There are always food trucks and live music there as well, so be prepared for the crowds.  Back in town, be sure to visit the fantastic shops that line the streets.  There are lots of local artists and when it comes time for supper, there are no bad choices.  With a restaurant on basically every corner, you are sure to have a great meal no matter where you choose. 

Each of the Cape Cod’s 15 towns and islands is unique and beautiful. All of them have pristine shorelines, historic sites, delicious restaurants, and wonderful shops. Chatham has a delightful Main Street, filled with unique stores and some of the best restaurants on CapeCod. Chatham is perfect for walking to town and offers many public beaches. You can spend the day lounging on the beach at Lighthouse Beach (1.2 miles from the Inn), Harding’s Beach (3 miles from the Inn), and Oyster Pond beach (a short 5-minute walk from the Inn). At night the town comes alive with many bars with live music, outdoor exhibits, and comforting summer breeze. Come to see the sights, explore the natural beauty of Cape Cod, and be pampered at The Old Harbor Inn. Book today at The Old Harbor Inn!

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