Top Activities & Attractions You Must Experience

If you’re planning a full day of outdoor fun, let us pack you a picnic basket to enhance your outdoor experience.

The outdoor activities listed below are all a short drive or walk from the inn.

Biking

This is an exceptional area for biking. The Cape Cod Rail Trail follows a former railroad right-of-way for 22 miles through the towns of Dennis, Harwich, Brewster, Chatham, Orleans, Eastham, and Wellfleet. Its paved surface and few hills make it ideal for cyclists. There are many opportunities to get off the trail and visit a beach. Food and water are readily available, and public restrooms can be found at Nickerson State Park, Salt Pond Visitors Center at Cape Cod National Seashore, and the National Seashore Headquarters. If you do not have a bike, bike rentals are available at many points along the way. We highly recommend The Little Capistrano Bike Shop in Eastham. The shop is located at the heart of Cape Cod Biking between The Nauset National Seashore Trail and The Cape Cod Rail Trail. You can also rent bikes in Chatham from Chatham Hood Bikes and Wheelhouse Bike.

Walking

If you enjoy walking, you are definitely in the right place. There are 11 self-guided trails along the Cape Cod National Seashore, Monomoy Wildlife Refuge, and the Wellfleet Bay Sanctuary. Furthermore, our premier downtown location makes it easy to enjoy everything that Chatham has to offer within walking distance. Read more in this Walking Guide in Downtown Chatham.

Hiking

If you are interested in hiking, there are short hikes within easy reach of the inn (Harding’s Beach Trail, Honeysuckle Lane, Frost Fish Creek Trail, Barclay Ponds Trail). In addition to great trails, Cape Cod has amazing views in the form of seascapes, salt marshes, and sand dunes. Many beaches and their associated trails have entrance fees for daily visitors as well as summer passes in season. Be sure to ask us about them before you head there.

• Cape Cod National Seashore
• Monomoy National Wildlife Refuge
• Nickerson State Park

Golf

Cape Cod’s pristine and scenic courses are a great way to stay active and decompress. Cape Cod is one of the top golf destinations in the Northeast.  Whether you’re just beginning or a scratch player, Cape Cod’s 27 public courses and 15 private facilities run the gamut of skill levels. Well-manicured fairways and greens beckon golfers to the area, as does the region’s mild climate, which often allows golfers the unique opportunity to play 52 weeks a year. These three public golf courses are within a short drive from The Old Harbor Inn:

• Chatham Seaside Links, Chatham
• Cranberry Valley Golf Course, Harwich
• The Captains Golf Course, Brewster

Tennis

There are several tennis courts located in Chatham, which are open to the public free of charge. Chatham High School: Turn left out of the driveway, take the first exit at the rotary and continue down to the traffic light. Make a right turn on Crowell Road. The High School is about ½ mile on the left.
Depot Road Courts: Turn right out of the driveway, make the first left on Depot Road, and the courts will be on your right.

The island is relatively small, a mere 14 miles long and 3.5 miles wide, but includes some 800 pre-Civil War-era homes, many of which have now been transformed into fine restaurants, inns, museums, and one-of-a-kind boutiques.

There are more than 80 miles of beaches on the island and acres of preserved and protected lands. You can wander the village, pop into a shop or two, try a local restaurant, rent a bike, go to the beach, or take a tour of the island. Do not forget to visit the Whaling Museum and Nantucket Basket Museum. This island can easily be explored in one day – however, we suggest that you plan ahead so you can make the most of your time on the island. There are several ferries to reach the island. The schedule and fares vary by time of year. Cape Air also flies daily to and from the island.

From Hyannis:
The Steamship Authority or Hy-Line – choose from a high-speed (1 hour – passengers only) and traditional ferry services (2 hours and 15 minutes – car and passengers).

From Harwich Port:
Freedom Cruise lines operates an express service (80 minutes – passengers only)

Once on the island, we recommend Gail’s Tours as a way of getting an overview of the island. Gail Nickerson grew up on the island and her hour-and-a-half tour is fun and informative.

Martha’s Vineyard

Martha’s Vineyard has five distinctive towns and is much larger than Nantucket. Located just seven miles off the coast of the Cape, Martha’s Vineyard is just a 35-minute ferry ride from Woods Hole. This 110-square-mile triangle is a little bit funky, a little bit “colorful,’’ and a little bit “farmy,” which makes it a top destination to visit in the summer. The western end, known as up-island, is more rural and wild than the eastern, down-island end, which includes the most visited Vineyard Haven, Oak Bluffs, and Edgartown.

From Woods Hole:
The Steamship Authority operates service to Oak Bluffs (45 minutes – passengers only) and Vineyard Haven (45 minutes – cars and passengers)
Once on the Vineyard, Island Transport operates a two-and-a-half-hour tour from Oak Bluffs, and there is also bus service from Vineyard Haven and Edgartown.

Whale Watching

A visit to Cape Cod would not be complete without a trip to P-Town (Provincetown) and a Whale Watch. We highly recommend Dolphin Fleet Whale Watch, as they have partnered with the Provincetown Center for Coastal Studies which provides naturalists for each trip. They are very informative and add to the enjoyment of the experience. The Whale Watch runs between May and October, and advanced reservations are recommended in the summer months. The trip lasts three to four hours.