With dozens of beaches, hundreds of charming shops and some beautiful homes, it’s hard to point out just one great location on the Cape. However, some of the most exclusive areas of Cape Cod are appreciated for their extreme luxury and privacy.

Chatham

Chatham is said to offer one of the Cape’s most scenic golf courses. Eastward Ho! Country Club dates back to the 1920s and is known today for its ultra-exclusive membership. It’s not easy to become a member and the dress code at the golf club is strictly enforced.

For luxury dining and hospitality, Chatham Bars Inn actually features four restaurants and two private dining rooms. It also includes a private beach with cabanas, daily boat shuttles, swimming and more. 

West Yarmouth

West

If you’re looking for a great way to experience the best scenery on the Cape, one way to do it is to hop on the Cape Cod Rail Trail. Running from Yarmouth to Wellfleet, the trail follows an old railroad right-of-way.

At 25.5 miles long, the paved trail is relatively flat, well-marked, and is said to be a great experience for those of all ages and experience. Bicyclists, walkers, runners and even horseback riders can use the trail.

To understand the history of the Cape Cod Rail Trail, though, you need to step back in time. During the 1800s it was extremely difficult to reach Cape Cod. That began to change when railroad tracks connected up Boston to Provincetown, leading visitors from places like Boston, New York and Connecticut to the Cape.

Photo: Historical Society of Old Yarmouth

While Cape Cod is filled with charming homes, shops and beaches, its history cannot be overlooked. Some of the Cape’s most notable landmarks date back centuries, including its many sea captains’ homes. A great place to get a better look at some of the homes is by taking a drive down Route 6A. From stately Colonials to modest Capes, you’re sure to find some lovingly restored homes, some of which date back to the 1600s.

The Captains’ Mile is where you’ll find more than 50 homes once owned by sea captains. They’re all identified by a distinctive gold and black Schooner Plaque outside.  While mostly privately owned today, we know they were once owned by sea captains because they’ve been awarded the special

Whether sailing, kayaking, fishing or lounging on the sand, Pleasant Bay presents a wealth of options for Cape Cod visitors and locals alike. Close to Harwich, Chatham and Orleans, the bay is extremely popular with visitors to both Nauset Beach and Barrier Beach.

As Cape Cod’s largest saltwater estuary, Pleasant Bay has likely been known by many names over the years. It’s believed Native Americans once called the protected waterway Monomoyick Bay, while an early explorer referred to it as Manamock. It took about a century more for the current name of Pleasant Bay to emerge.

To this day, though, Pleasant Bay continues to live up to its most current namesake, a relaxing and peaceful location that’s inspirational to all who visit. It’s also a great

Serving students of Chatham and Harwich, Monomoy Regional High School in Harwich continues to be a shining example of new technology and innovative ideas for success. A project more than a half century in the making, the new regional high school officially opened just a few years ago, serving more than 600 students in 8th through 12th grade.

Now part of the Monomoy Regional School District, the building is the only high school in the district, fed by the Harwich and Chatham Elementary schools plus Monomoy Regional Middle School. It wasn’t an easy solution, though, for either community.

In fact, it took decades for town leaders to come up with an agreement, reached by voters in 2010. It then took $49 million to complete the vision, funded by tax money

Sometimes referred to simply as “The Port” by locals, Harwich Port is actually three harbors worth of fun. Home to the Saquatucket, Allen and Wychmere harbors, it’s easy to get out on the water here, with various boating tours available for those of all ages.

A popular spot for vacationers, Harwichport is home to both the private Allen Harbor Yacht Club and home to the Wychmere Beach Club. You’ll find tennis, docks and moorings at Allen Harbor, although the harbor’s primarily reserved for yachting. This location is said to be best for small craft due to its narrow entrance.

Wychmere Harbor, meanwhile, offers moorings for powerboats and sailboats. It also boasts a pier and a park for the enjoyment of locals and visitors.

The most diverse harbor in Harwich

Several Cape Cod communities are banding together to help protect Pleasant Bay now, and for years to come. The towns of Chatham, Brewster, Orleans and Harwich all share its watershed.

Just recently they joined together, gaining issuance of the first Watershed Permit ever in the state. While it may seem that everything came together in recent weeks, it’s actually been a work in progress for a couple of decades.

That’s when the four towns first adopted a Pleasant Bay Resource Management Plan, and began implementing it via the Pleasant Bay Alliance. The new permit, however, specifically outlines all of the measurable steps the towns plan to take together and individually, all aimed at addressing threats to the health of the Bay.

With it, the towns are

Family-friendly entertainment is on tap all summer long with live music strolls in both Chatham and in Harwich Port. While the tradition has been a long-standing one in Harwich, the fun just spread to Chatham this summer season.

Dubbed Mondays on Main, the new Chatham addition brings musicians, bands and other types of live entertainment to Main Street. The Monday evening event stretches for eight weeks this summer, from locations including the Chatham Wine Bar to the rotary, and features a variety of themed nights designed to especially appeal to families.

Entertainers are stationed in courtyards, on lawns and on patios just off the main sidewalk to encourage visitors to enjoy the entire area. The idea is to give people a fun and unique way to

Improvements are well underway at Saquatucket Harbor, where crews aim to start in on a waterside reconstruction project within just days. For weeks now, crews have been busy removing piles and finger piers in anticipation of the start of the larger project of fixing up the harbor.

Saquatucket Harbor services commercial, recreational and charter vessels, as well as ferries. Local leaders say the docks were in real need of replacement, though. At 40-years old, the docks were considered unstable, so plans were made to fix the issues, broken up into landside and waterside projects.

Planned improvements include dredging and then constructing a new, ADA compliant dock; including nearly a dozen more slips than the area has had in the past. The waterside

Affluent Harwich Port is no longer simply a celebrated location of residents and visitors, but is now getting top honors for its Main Street, nationwide. The village was just recognized for playing host to one of America’s best main streets.

According to Country Living magazine, the Harwich Port Main Street lands at number 21 on its list of the top 23 small town main streets in the entire nation. It’s the only Cape Cod town to make the list, and one of just a handful of locations in New England. The publication acknowledges it chose Harwich Port for everything from great food to vendors and live music.

The new ranking should come as no surprise, for the area was also declared the second ‘Happiest Seaside Town’ for 2016, as designated by Coastal