Photography by Shutterstock.com/Mark Yarchoan • Brant Point Lighthouse

Many visitors to Nantucket feel that when they step off the ferry, they are taking a step back into history. And with good reason! The cobblestones lining the roads downtown were brought here in ships; the island—affectionately known as The Gray Lady—is dotted with historic sights such as the Old Mill and the Nantucket Atheneum; and most island homes feature grays and white, the colors of tradition and calm. To cement the image, the entire island was named a National Historic Landmark in 1975.

Learn more about the island’s history at the Nantucket Whaling Museum, or pay a visit to the island’s three historic—and very attractive—lighthouses. The Nantucket Shipwreck & Lifesaving Museum also offers information on the more than 700 ships that have wrecked over the years in Nantucket waters.

Another historic spot, Main Street Square, bustles with art galleries, gift shops and great restaurants. Stop in one of several lightship basket merchants to browse one of the island’s famous creations. Get a feel for how the locals live by slipping on a pair of Nantucket reds; Murray’s Toggery Shop offers a colorful selection. Nearby, the Dreamland Theater on South Water Street offers a lively schedule of films, opera simulcasts and other unique events.

A great way to explore different parts of the island—from Madaket to Siasconset—is by bike, as Nantucket has more than 30 miles of bike paths and several great rental shops. The island’s narrow roads and massive homes are beautiful, and there are flowers and quirky quarterboard signs everywhere.

Photography by Josh Shortsleeve • Main Street Square

En route, stop for a sandwich or snack at Bartlett’s Farm, or enjoy a sweet ice cream at the Juice Bar on Broad Street. Another great spot for a bite is Barcos y Tacos, which offers tasty breakfast tacos and burrito bowls on Sanford Road.

Staying here? For a one-of-a-kind experience reserve a room at the luxurious White Elephant, a hotel famous for its airy suites and wonderful views of the harbor.

Not to be missed, Nantucket has a boatload of beaches, including Jetties and Surfside. For refreshment of a different sort, Cisco Brewers is the perfect spot to take in some great live music, fresh island air and a locally brewed beer!

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Photography by Shutterstock.com/StevensonChung • Ocean Park, Oak Bluffs

A mecca for tourists, a retreat for presidents and the home of Island Alpaca, The Black Dog and Jaws—the 1974 thriller was famously filmed here—Martha’s Vineyard is a short ferry ride from both Woods Hole and Hyannis . . . and a very special place.

At just under 100 square miles, the Vineyard is comprised of six towns, each with its own unique history and culture. Visitors arriving aboard the Island Queen from Falmouth commence their stay in Oak Bluffs. Circuit Avenue, the town’s main thoroughfare, is lined with shops and restaurants, and it’s hard to miss the free-spirited vibe. Stop in Murdick’s Fudge for a quarter-pound of chocolate, rocky road or Cape Cod cranberry.

Next up, stroll through the remarkable gingerbread houses. Numbering more than 300, the cottages date back to a religious camp meeting community in the mid-1800s and are dolled up in pastel colors and creative cutouts. Another must-visit is the Flying Horses Carousel. Take a nostalgic ride—and try to capture the brass ring—on the country’s oldest platform carousel.

Dining in Oak Bluffs? Sink your teeth into a burger or burrito at Sharky’s Cantina, or try the steak and seafood at The Martha’s Vineyard Chowder Company. Another great island restaurant is Menemsha’s Beach Plum Inn, which creates its menu from scratch each day—utilizing fresh local ingredients.

Photography by Noah Wiehe • Gay Head Lighthouse, Aquinnah

Surrounded by water, the Vineyard has a bevy of wonderful beaches. South Beach (a.k.a. Katama Beach) in Edgartown faces the Atlantic; and on the west of the island, Aquinnah Public Beach offers amazing views of the region’s red clay cliffs.

Additional island attractions include The Martha’s Vineyard Museum in Edgartown—a great place to explore the island’s rich history—the recently re-settled Gay Head Lighthouse and Alley’s General Store, a popular West Tisbury market that offers snacks, sundries and souvenirs.

Staying longer? Check out the many miles of island bike trails, or board the On Time II ferry to Chappaquiddick; there, visitors will discover the peaceful MyToi Garden and the Cape Poge Wildlife Refuge, a swath of pristine land featuring a lighthouse, a lengthy beach and captivating scenery.

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Photography by Chuck Anzalone • Commercial Street Summer

Located on Cape Cod’s outermost tip, Provincetown is a vibrant community with a fascinating history, a colorful arts scene and some great shops, restaurants and beaches. The town is famous for its gay community, which celebrates at several unique annual events including the Carnival festival in August and Holly Folly in December.

In November of 1620, the Mayflower set anchor in Provincetown Harbor and the Pilgrims explored this Outer Cape area before permanently settling across the bay in Plymouth. To commemorate this visit, the Pilgrim Monument, which stands 252-1/2 feet atop High Pole Hill, was completed in 1910. Climb to the top for some exercise and a spectacular view.

Since the late 1800s, Provincetown—with its pastel sunsets and ethereal natural light—has been a haven for artists of all stripes. For most of that time—it was founded in 1914—the Provincetown Art Association & Museum has honored these individuals, and the museum hosts exhibit openings and other events throughout the year. All along Commercial Street, galleries such as Kobalt Gallery, Gallery Voyeur and many more showcase the work of prominent and local artists.

A peaceful walk in winter, Commercial Street explodes with activity in summer, and visitors will find eye-catching shops selling everything from clothing, candy and ice cream, to custom hammocks, fishing gear and P-town souvenirs. Don’t miss the intoxicating scent of incense emanating from Shop Therapy, which offers a nice collection of tapestries and beads.

Photography by Shutterstock.com/HaveSeen • Provincetown Harbor

Commercial Street offers endless dining options, sure to please any palate. A landmark, the Lobster Pot is beloved for its fresh local seafood; The Central House at the Crown & Anchor features a well-marbled menu prepared by a well-known chef; and Kung Fu Dumplings offers a selection of Chinese favorites. Hungry for more? Try the grilled PB&J—featuring homemade peanut brittle and strawberries—at The Canteen, or a lobster roll at The Burger Queen.

Surrounded by water, Provincetown has many natural attractions to explore. Take in some rays at Race Point or Herring Cove Beach; cycle along trails in the scenic Province Lands; or set out on a whale watch in hopes of seeing a leviathan or two, first-hand.

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Photography by Doug Lemke • Highland Lighthouse

 If you’re looking for peace and quiet, you have come to the right place. More than half of the land in Truro lies within the Cape Cod National Seashore and, as locals know and visitors will soon become aware, there are no fast food restaurants or even stoplights here. There is, however, a lot to do, see and enjoy.

Surrounded by water to the east and west, Truro has a number of big-wave beaches including Ballston and Head of the Meadow, both facing the Atlantic. At low tide, visitors to the latter can occasionally view the remains of the Frances, a ship that wrecked off the coast in 1872. Get a better view of the water aboard one of the many local fishing charters, which set out from Pamet Harbor.

Aiding ships at sea for more than 200 years, Highland Light is the oldest lighthouse on Cape Cod and a spectacular sight to behold. A stone’s throw away, the Highland House Museum resides in a former hotel built in 1907. Run by the Truro Historical Society, the museum displays artifacts detailing the lives of early settlers in the area, and is open daily, June to September 30.

Photography by Ken Schulze • Days’ Cottage

Those staying in town have a variety of options. First, sweetness and tranquility are assured at Shady Rest Cottages on Route 6, and The Gingerbread House on Depot Road. Just need a bed? Hostelling International-Truro offers basic accommodations  in a former Coast Guard Station. There are three campgrounds in town, too! Lastly, fulfill a dream by staying for 24 or 48 hours at one of the famous Days’ Cottages.

Truro has a flourishing arts scene, and visitors will find a number of small galleries and studios. Most of the work created at Jobi Pottery includes a nautical twist such as an animated sea creature or fish. Another local gem, Truro Vineyards is a great spot for weddings and offers tastings and tours. Sample 13 different varietals—and a new spiced rum—and bring home a red or white in the vintner’s unique lighthouse-shaped bottle.

For lunch or dinner, Savory and the Sweet Escape offers a plethora of pizzas and paninis; and remember to save the turtles—save room for the turtles, that is!—at the Chequessett Chocolate Factory & Café.

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Photography by Christian Delbert • Uncle Tim’s Bridge

There are several common threads running through Wellfleet. First, the Outer Cape town offers a thriving scene for the arts with many galleries and popular venues for both theater and cinema. There’s also a strong sense of community here as residents and visitors alike turn out in droves to celebrate at OysterFest, Restaurant Week and other annual events. And stretched as it is between the Atlantic and Cape Cod Bay, the flavor of Wellfleet and its people has been continually seasoned and shaped by the sea.

Great for walking, Main Street is a charming village with gift shops, eateries and galleries galore. A popular community center, Preservation Hall occupies a former church building and hosts concerts, weddings and the Wellfleet Farmers Market! For coffee and sweets, pop in PB Boulangerie Bistro, the aromatic home of freshly baked breads, cookies and apple tarts. For another Main Street treat, enjoy a meal at Winslow’s Tavern. For starters, the tavern prepares oysters in several delicious ways, including lightly brushed with a Tabasco-lime butter. Wash them down with a drink they call the Porch Swing.

Photography by Amanda McCole • Cahoon Hollow Beach

Other spots to savor some seafood include Catch of the Day on Route 6, Mac’s on the Pier, and The Beachcomber of Wellfleet—a summertime signature overlooking Cahoon Hallow Beach. A hotspot on summer nights, the Beachcomber has it all: dancing, drinks and unbelievable views. To the south, Marconi Beach, named after Guglielmo Marconi who sent the first trans-Atlantic wireless message to England from this area, offers a 1-1/2 mile walking trail and an observation platform providing fantastic sightlines of the coast.

Speaking of sightlines, The Wellfleet Harbor Actors Theater has been entertaining audiences since 1985. In addition to dramas and comedies, in 2016 the theater has put together a beefy schedule of opera screenings; the shows are simulcast from New York’s Metropolitan Opera House. Seeing a film beneath the stars at the Wellfleet Drive-in is another popular tradition. Grab some snacks, load up the car and make your way to a double feature.

Additional attractions in this coastal community include the rigorous trails of Great Island, the 1,100-acre Wellfleet Bay Wildlife Sanctuary—great for bird watching—and Uncle Tim’s Bridge, a scenic span that crosses Duck Creek. Should you find yourself in a sudden auto locksmith emergency situation, 24/7 Car Locksmiths are here to assist you with all your car security needs.

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Photography by The Dune Tramp • Eastham Windmill

 The town of Eastham—located on the “forearm” of the Cape Cod peninsula—has a fascinating history and over the years has been a community where fishing, farming and creative expression have flourished.

Eastham residents take pride in their history, and several local landmarks help tell the story. For starters, the town boasts several connections to the Pilgrims: First Encounter Beach on Cape Cod Bay is the site where the Mayflower passengers and Native Americans first met in 1620; also, three Pilgrims are buried in Eastham’s Cove Burying Ground. The 1869 Schoolhouse Museum offers a glimpse into the more recent past as local students were taught in this one-room school through 1936. View the original headmaster’s desk and other town treasures.

Nearby, Nauset Light, which is located within the Cape Cod National Seashore, is a hugely popular attraction. Tours, including a climb to the top, are offered on Sundays, from June to September. Located on the Cape’s Atlantic-facing coastline, Nauset Light Beach and Coast Guard Beach—beloved by writers Henry David Thoreau and Henry Beston—are wonderful spots for walking, swimming or simply to observe nature. Be on the lookout for seals frolicking in the surf.

Nauset Lighthouse

For many, Eastham’s Fort Hill area is synonymous with nature and tranquility, and the Fort Hill Rural Historical District offers walking trails through 100 acres of former farmland. Consider staying at Fort Hill Bed & Breakfast, operated out of an 1864 farmhouse.

Open daily year-round, the Salt Pond Visitor Center at 50 Nauset Road offers information about the region’s geology including a large topographical map of the area’s glacial history. Displays also inform of the area’s Wampanoag history, whaling and the lifesaving service. Outside, a 1.5-mile trail offers scenic views of the Nauset Marsh.

Time for a snack? Visit The Hole in One Donut Shop on Route 6 for coffee and donuts in glazed, filled and dipped varieties. Later, enjoy a meal at Arnold’s Lobster and Clam Bar. The line is often out the door—but for good reason; the food is wonderful, and Arnold’s is a perennial winner in CAPE COD LIFE’s “Best of” contest for its succulent lobster rolls, fried clams and more!

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Photography by Richard Del Gallo • Nauset Beach

Beautiful, classy, historic and relaxing: these are some of the terms that come to mind when pondering the town of Orleans.

Whether you’re taking in the sunset at Rock Harbor, wading along the tidal flats off Skaket Beach, or simply enjoying the soft sand and pounding surf along Nauset Beach, Orleans’ natural attractions amaze.

Regarding manmade marvels, The Orleans Waterfront Inn is a captivating hotel located in a very special place—overlooking scenic Town Cove. Another stately structure, the Captain Linnell House on Skaket Beach Road, is a popular wedding venue, and in the restaurant diners can enjoy oysters, salmon, duck and lamb.

Other dining options to savor in town include The Lobster Claw and Land Ho!, or Nauset Farms on Main Street which offers sandwiches and homemade chips. Bonus: try the Nauset Bomb, a giant muffin covered in cinnamon and sugar! Another sweet spot is the Hot Chocolate Sparrow, which features a robust menu of coffees, baked goods and of course, their famous hot chocolate!

One quirky town staple is the Bird Watcher’s General Store on Route 6A; inside, visitors will find birdfeeders and guides as well as avian-themed crafts and jewelry. The Orleans Farmers’ Market also draws a crowd on Saturday mornings beginning in May; check them out at 21 Old Colony Way!

Photography by Jennifer Dow • Jonathan Young Windmill

For the uninitiated, Orleans’ history is loaded with riveting events including attacks on the town by two foreign powers, one during the War of 1812 (at Rock Harbor) and the other in World War I (at Nauset Beach). Learn about these and other stories at the Orleans Historical Society Meeting House Museum, the French Cable Station Museum and at the magnificent Church of the Transfiguration.

Orleans is also a haven for artists, and the renowned Addison Art Gallery features the work of more than 20 talented locals. In 2016 the gallery is displaying the work of artists inspired by the late Edward Hopper and several events are scheduled. Finally, complete a perfect summer day with a visit to Eldredge Park, home of the Cape League’s Orleans Firebirds. If baseball is an art form, this field—and the entire game day experience—is a masterpiece.

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Chatham Lighthouse

Tucked in Cape Cod’s southeastern corner, Chatham is a popular spot for many reasons: from stunning scenery and great locally caught seafood to a charming downtown area and the luxurious Chatham Bars Inn, this town has it all!

Most visitors head straight to Chatham Light, which overlooks North Beach, Lighthouse Beach and the Atlantic beyond. First constructed in 1808, Chatham Light has seen a lot of change over the years; first, the original light towers were replaced twice in the 19th century and moved back from an eroding cliff; then in 1923 Chatham’s Twin Light—yup, for more than a century there were two!—was moved to Eastham to become Nauset Light. Today, the area is popular year-round, and coin-operated telescopes offer great views of the local seal population.

For an up-close look at the lives of Cape Cod fishermen, head north to the Chatham Fish Pier to watch dozens of local boats bring in the day’s catch of haddock, halibut and lobster. The seafood is distributed to local businesses, including the nautically themed Chatham Squire on Main Street. The cozy restaurant offers a seafood menu to savor, and for those who can’t decide, the Chatham Cioppino is chock full of fish, scallops, mussels and more.

Photography by Lynne Albright • Chatham Fish Pier

Main Street offers several blocks of specialty shops and cafes; it is a great place for a walk any time of day. Be sure to pop in to Chatham Candy Manor for chocolate-covered cranberries and other sweets; Yankee Ingenuity, which offers a one-of-a-kind collection of gifts; and Blue Water Fish Rubbings, a unique boutique that utilizes real fish and shellfish—and the Japanese technique of gyotaku—to create printed t-shirts, blankets and more.

The art scene in Chatham is one of the most predominant on the Cape, and galleries abound on Main Street. Chatham Fine Art, The Hearle Gallery, the Nickerson Art Gallery and others display the work of creative masters and local artists. For a lasting image of this coastal community, drive along Shore Road to see the world famous Chatham Bars Inn, an architectural wonder overlooking the ocean.

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Photography by Elizabeth Menser • Pleasant Lake

Located along Nantucket Sound and featuring a topography that includes ponds, harbors and flatlands, the town of Harwich is often referred to as the birthplace of the Cape’s cranberry industry. During the mid 19th-century, Alvin Cahoon established in Harwich the nation’s first commercial cranberry bog, and many bogs are still in operation today. The town celebrates this fruity connection every September with the annual Harwich Cranberry Arts & Music Festival in Brooks Park. Learn more by taking a Cape Farm and Cranberry Company bog tour—or play a round or two at the sweet Cranberry Valley Golf Course.

Harwich is also blessed with scoop after scoop of another tasty product: ice cream! The family-owned Sundae School Ice Cream offers homemade flavors including Bass River Mud and Crème de Menthe Chip. Just up the road, the similarly named SchoolHouse Ice Cream and Yogurt is another sweet spot for a cone, offering super premium flavors like Red Velvet Cupcake and Peanut Butter Madness.

Harwich has great dining options as well. L’Alouette, a quiet French bistro on Route 28, combines fresh Cape seafood with traditional French cooking. Another savory option on 28 is Land Ho! Harwichport. Enjoy the artwork on the walls, a beer at the bar and a selection of sandwiches, steaks and seafood entrees. To really treat yourself, reserve a table at Twenty- Eight Atlantic at the Wequassett Resort & Golf Club. The restaurant continually wins awards in CAPE COD LIFE’s annual “Best of” contest, and the view overlooking Pleasant Bay is spectacular.

Photography by Jean Chisser • Wychmere Harbor

Now—for some exercise! Grab your bike or walking shoes and hop on the Cape Cod Rail Trail, which travels through Harwich from Dennis to Brewster; the Old Colony Rail Trail continues the fun all the way to Chatham. There are also many great hiking areas in town—more than 700 acres! The Harwich Conservation Trust has detailed trail maps and offers guided walks and other events during the year.

Want more? Harwich is home to two longtime performing groups: the players of the Cape Cod Theatre Company (formerly Harwich Junior Theatre), who put on colorful year-round performances; and on a different stage, the Harwich Mariners of the competitive Cape Cod Baseball League.

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Photography Judith Keneman • Paine’s Creek

Named for Elder William Brewster, a Mayflower passenger and one of the Pilgrim’s first religious leaders, the town of Brewster is a mecca for nature lovers and outdoor explorers.

For starters, locals and visitors flock to Nickerson State Park, a 1,900-acre camping area that offers hundreds of campsites, and eight miles of trails through wooded areas and along glacier-formed kettle ponds. A great option for bikers and walkers is the Cape Cod Rail Trail, which cuts through the park and features 22 miles of paved trails from Dennis to Wellfleet. Nearby, the Cape Cod Museum of Natural History always has fascinating exhibits on bees, birds and other wildlife—as well as a peaceful salt marsh trail.

Brewster is also blessed with a bevy of great beaches overlooking Cape Cod Bay. Breakwater and Paine’s Creek Beach are cozy spots to take in a sunrise, while Crosby Landing Beach is within walking distance from the state park and features a nature trail and boardwalk. At most of these beaches, Brewster’s famous tidal flats stretch out for quite a distance at low tide, creating opportunities for wading and exploring tidal pools.

Stony Brook Grist Mill

Down the road, another attractive scene is the Ocean Edge Resort and Golf Club. Featuring the spectacular Nickerson Mansion—a Brewster landmark—Ocean Edge offers top-notch accommodations and dining options. Great restaurants in town include The Brewster Fish House—a must-stop for lunch, dinner and calamari. Want something sweet? Try the Hopkins House Bakery on Main Street, a laidback eatery that serves tasty scones, strawberry muffins and more, baked fresh every day. Why not pick up a few and savor them down the road on the relaxing grounds surrounding the Stony Brook Grist Mill.

Finally, no Brewster visit is complete without a stop at the Brewster General Store. The historic structure on Route 6A, which once was a church and has also served as a post office, offers a large variety of snacks and souvenirs to remember your stay, from postcards and puzzles, to Christmas ornaments and coffee mugs.

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