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Couples Getaways
(No children under 12)

Pet Free Facility

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Top Activities & Attractions You Must Experience

Plan Your Stay with the Best Things To Do in Chatham, MA

Located on Cape Cod in Massachusetts, Chatham is a little seaside village brimming with quaint beauty and charm. Time slows down and life feels simpler while you are here. Travelers of all kinds enjoy the town for its attractions as well as the rejuvenating atmosphere. Chatham is home to a bounty of things to do and see, from coastal adventures to unique dining experiences, and everything in between. Whether you enjoy outdoor activities, shopping, or exploring the National Seashore, there is truly something for everyone. Day trips to Martha’s Vineyard or Nantucket are another guest favorite. Check out the list below to start planning your trip to The Old Harbor Inn today!

Stay in the Heart of Chatham

The Old Harbor Inn in Chatham, MA is centrally located to explore and experience all the many Cape Cod activities available to our guests. We also offer concierge services to help you plan your day. Our comfortable rooms, delicious breakfasts and afternoon refreshments are swooned over by our guests. Plus, with our enhanced cleaning and safety procedure, and our flexible cancellation policies, you can be confident in your lodging choice. We can’t wait to host your next getaway and help you get ready to enjoy your “Endless Summer.”

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The Best Chatham Beaches

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Chatham has some of the most beautiful and secluded beaches on Cape Cod. There are many options to choose from without leaving Chatham.

Six major saltwater beaches with views of Nantucket Sound and the Atlantic Ocean are within a short walk or drive from The Old Harbor Inn. The most scenic by far is Chatham Lighthouse Beach.  We invite you to come and explore these and all the other beaches that Cape Cod has to offer.

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Water Activities

Fishing, Boating & Kayaking

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Known as one of the top fishing destinations on the East Coast, the angling adventure of a lifetime awaits you on Cape Cod!

Striped bass, bluefish, flounder, mackerel, red snapper, and yellowfin tuna are just a few of the amazing catches you can find in Cape Cod waters. The fishing season typically runs May through October, and there are many fishing charters to choose from.

There are many options for fishing on Cape Cod. Go to the Traveling Angler to explore a variety of fishing options.


Cape Cod’s more than 550 miles of shoreline and 40 miles of national seashore are what make it a premier boating destination. Many boat rides depart from the waters surrounding Chatham, and enjoying sunset tours, kayaking, sailing, seal & whale watching, paddle boarding and kitesurfing are great ways to explore Cape Cod’s waterways! Rent a power or sailboat and view Cape Cod from a whole new perspective.  Rent a stand-up paddleboard or kayak to explore the ocean, harbors, and kettle ponds on Cape Cod. Sit & relax while enjoying one of the eco tours and learn about the Cape’s marine life.

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Outdoor Recreation

Walking, Hiking, Biking, Golfing, Tennis

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If you love the outdoors, then you’ll love Chatham & Cape Cod! With a variety of outdoor activities, for all levels of nature lovers, you’re bound to find a way to enjoy the fresh air.

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.


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.


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.


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’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:


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.

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Art & Museums

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Cape Cod’s distinction as a cultural destination is owed largely to a compelling and colorful history, which has inspired a fascinating collection of museums over time.

Some of these – including the John F. Kennedy Museum and The Heritage Museum and Gardens – are among the region’s most popular visitor attractions. But the smaller, more intimate museums dotting the Cape’s landscape have an equally intriguing story to tell about the region’s rich heritage.

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Parks & Preserves

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No trip to Cape Cod would be complete without visiting some of the historic lighthouses. Overlooking the Atlantic Ocean, these Lighthouses give visitors the opportunity to learn more about Cape Cod’s history while enjoying beautiful ocean views.

Some of the lighthouses are still in use today, while others are historical landmarks open to visitors. Cape Cod and the Islands are home to 22 stunning lighthouses. That’s one of the highest concentrations of lighthouses in the U.S.!

The Old Harbor Inn is just a short walk from the iconic Chatham Light offering the most scenic ocean views, and it’s also just a short drive to Stage Harbor Light.

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Dining & Night Life

The Best Restaurants in Chatham

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When you think of Cape Cod the first two things that come to mind are beaches and seafood. You got that right! A trip to Cape Cod is not complete without indulging in a variety of fresh seafood.

Recognized as home to one of Cape Cod’s most prolific fishing fleets, Chatham is well known for its fresh fish and seafood. Chatham waters are a treasure trove of clams, oysters, lobsters, scallops, tuna, and cod. You will find restaurants ranging from clam shacks to fine dining that rival the best in New York City and Boston.

Fresh Seafood


Music & Theatre

Cape Cod boasts many theaters, with an exciting lineup of musical revues, Broadway productions and beloved classics.  Performances at the Cape Playhouse- America’s oldest professional summer theatre – attract some of the nation’s finest stage, television and film actors. The Cape Cod Symphony Orchestra is a polished and professional ensemble of 75 musicians. And Cape Cod Melody Tent is headlined by some of the finest popular musical and comedian acts!

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Chatham offers an exceptional number of unique high-end shops to satisfy any taste. Whether you are seeking an unusual souvenir, a T-shirt, fine art for your home, or jewelry for that special someone, you’re sure to find it at one of our many shops.

If Main Street does not satisfy your appetite to shop, Route 6A offers the largest concentration of antique shops while Wellfleet and Provincetown are home to numerous quirky galleries. The nearest mall is located in Hyannis and features several major department stores.

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White lighthouse on the beach with large building and water in the background

Day Trips

Day Trips

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This gorgeous island, with its preserved village of sea captains’ homes and bumpy cobblestone streets, is a day-tripper’s dream.

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.

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Stage Harbor


Oyster Pond

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Sutcliff’s Inlet

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