How to Spend a Weekend in Chatham, Cape Cod
Where to stay, eat, shop and unwind in Chatham, Cape Cod’s most charming and effortlessly chic town.
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Cape Cod offers something for nearly every type of summer visitor, whether you’re intrigued by the nightlife of Provincetown, the sleepy charms of Brewster, or the bustle of Hyannis Port. One town, however, stands out above all the rest—especially for the weekend traveler: Chatham, on the southeastern tip of the Cape. This historic fishing community dates back to 1664 and blends quintessential New England charm with a lively downtown and a thriving arts and culinary scene.
Though Chatham is ritzier than some of its neighboring communities, such as Brewster and Harwich, it still retains the rustic, laid-back charm that differentiates the Cape from the haughtier atmosphere of Nantucket. The walkable downtown, with its array of local boutiques, is reminiscent of Martha’s Vineyard’s Edgartown—no ferry ticket required. (Though Cape traffic can be brutal; we recommend hitting the road as early as possible to avoid a standstill on Route 6.)
A long weekend offers plenty of time for travelers to get a taste of all Chatham has to offer, particularly in the summertime, when the Cape Hydrangea Fest is underway, and you can catch a Chatham Anglers baseball game. Summer visitors can admire the Arts in the Park pop-up downtown, which showcases local artists between June and August, though there are also art galleries open year-round.
From where to get the best lobster nachos to the most idyllic place to watch the sunset, we’re rounding up the best spots to visit for a long weekend in Chatham. Read on and get ready to book your next Cape getaway.
The Chatham Travel Guide: The Best Restaurants, Best Beaches and Best Things to Do
Where to Stay
Chatham Bars Inn
- 297 Shore Rd, Chatham, MA 02633
Chatham Bars Inn is the pinnacle of Cape Cod luxury—a one-stop shop for cocktails, beaching, boating and fine dining. The oceanfront hotel offers some of the most gorgeous views on Cape Cod, with accommodations situated across 25 acres overlooking the sea. The property houses 217 rooms and suites, including 30 guest cottages for visitors who truly want to feel like summer residents. The decor is very Nancy Meyers: white linens, large French doors, classic coastal elegance. Book a spa treatment and choose from indoor or outdoor rooms—the cabanas in the Zen Garden are particularly blissful for a massage or facial. Sign up for a morning seal cruise, or a charter to Nantucket or Martha’s Vineyard. Other popular activities include shark safaris and whale-watching. Tennis courts are available at the resort for guests, with clinics for players of all ages and expertise. Finally, order the lobster nachos at the Beach House Grill, and watch the sunset from the Adirondack chairs at the Bayview Terrace.
Chatham Inn
- 359 Main St, Chatham, MA 02633
Five-star luxury awaits at the Chatham Inn, a Relais & Châteaux property on Main Street, just a quick walk to downtown shops and Lighthouse Beach. The boutique inn offers 18 rooms and suites, with cozy fireplaces, marble touches and spa showers. The retreat features classic Cape Cod coastal decor, befitting Chatham’s oldest operating inn, with wide-plank wood floors and seascapes by local artists. The on-site dining is spectacular, with an award-winning daily four-course menu offered year-round at Cuvée, with dishes that vary by seasonality. (Order the oysters whenever possible.) Book a three-hour Chef’s Table experience, where the cuisine is catered to your preferences, and opt in for the included wine pairings. Adirondack chairs provide the perfect perch for watching the sunset, and the fire pit is ideal for stargazing after a long day in the sun.
Ocean Edge Resort & Golf Club
- 2907 Main St, Brewster, MA 02631
For an equally historic property that’s a bit quieter, consider Ocean Edge Resort & Golf Club. It’s just outside of Chatham, in nearby Brewster. Originally a private home, the “Mansion at Ocean Edge” was built in 1890 as a summer estate known as Fieldstone Hall. The larger resort was built around the mansion in the 1980s and boasts enviable waterfront acreage. The interior design blends classic New England style with an opulent twist, incorporating the Renaissance Revival and Gothic touches that were present in the original 18th-century architecture. The resort’s private beach, Bay Pines, overlooks the Brewster Flats, and guests can set out on oyster tours in the early morning. Enjoy cocktails around the fire pit and head down to the Beach Bar for sunset drinks overlooking the water. Another option to consider is the Wequassett Resort & Golf Club in nearby Harwich Port. This 120-room property is spread out on 27 acres, with two tennis courts, pickleball courts, and, of course, the Cape Cod National Golf Club, which is ranked one of the top private courses in the country.
What to Do
Chatham Lighthouse
- 37 Main St, Chatham, MA 02633
A trip to Chatham is incomplete without a visit to the beautiful beach, so why not combine your sunbathing with some sightseeing? The Chatham Lighthouse is one of the more stunning historic landmarks on the Cape, and one of the few remaining 24-hour lighthouses in the United States. The Chatham Lighthouse Beach is right across the way and is famous for its sand dunes, shallow pools and low tides. Lighthouse Beach is popular with windsurfers, though the riptides make swimming a bit more difficult. Head to Harding’s Beach in South Chatham to take a dip in the water (there are lifeguards here), and potentially go clamming—a popular Cape activity, though permits are required, so check the local regulations. Lastly, be shark-aware when swimming off Chatham, and check the warning signs posted on the beach—but more on that below.
Whale Watching
- 297 Shore Rd, Chatham, MA 02633
While the shark sightings off the Cape may have gotten all the attention as of late, we suggest heading out to sea on a whale-watching tour. There are a few options, including one via Chatham Bars Inn. You don’t need to be a guest of the resort to book a charter, and though the focus is on humpback whales, there’s a chance to spot minke and pilot whales, whale sharks and more. Whaling was a major source of industry on the Cape in the 18th century, though by the mid-19th century, this shifted towards tourism. Today, you can spot the whales during peak migratory season from May through October. And, if it’s Jaws you’re after, look into great white shark charters, also offered by Chatham Bars Inn.
Explore the Walking and Biking Paths
For a land-based activity when you visit Chatham, consider checking out the Cape Cod Rail Trail. The 25.5-mile paved path runs from Yarmouth through Wellfleet, offering picturesque views of the coast and seaside. It doesn’t technically run directly through Chatham, but there is a side loop that connects it. As for walking trails, consider the two-mile Harding Beach Point or the 1.5-mile Morris Island Loop at the Monomoy National Wildlife Refuge, a scenic haven for birdwatchers. You can also stroll through one of the 11 trails at the Cape Cod National Seashore. Another option is to simply enjoy views of the harbor and the fishing boats while strolling the Chatham Fish Pier, which is particularly picturesque at sunset.
Where to Eat
Del Mar Bar & Bistro
- 907 Main St, Chatham, MA 02633
Del Mar is a classic dinner choice downtown, with a lively crowd filing in on summer weekends for the local seafood, pasta and wood-fired pizza. Unlike many Cape Cod establishments, the restaurant operates year-round, aside from a brief closure in January. Open every day aside from Sunday, reservations are recommended, especially during peak season. Popular dishes include the halibut, filet mignon and oysters Rockefeller. The drinks menu offers a spirited selection of creative cocktails, but we recommend the Malaysian Margarita, and for dessert, the vanilla bean crème brûlée.
Bluefins Sushi & Sake Bar
- 513 Main St, Chatham, MA 02633
Bluefins is the perfect downtown hideaway to grab cocktails and rolls while sitting at the bar before heading out for a night on the town. The sushi is spectacular and the martinis are mouthwatering at this stylish eatery on Main Street. Bluefins prioritizes local ingredients and sources from Cape Cod farms for its modern Asian cuisine. The restaurant is open year-round, and reservations are not accepted between Memorial Day and Labor Day—arrive early during peak season to secure a table. The martini bar is a favorite local spot; expect a lively, sophisticated ambiance with warm, intimate lighting ideal for a date night. The menu features hot dishes alongside delectable sushi offerings; the Cape Cod Monster roll and the Tornado roll are favorites. Although the cuisine is primarily Japanese, Thai and Korean dishes are also available, as are vegetarian options.
Buffy’s Ice Cream
- 456 Main St, Chatham, MA 02633
A summer weekend on the Cape is incomplete without a visit to Buffy’s, the iconic purveyor of the only homemade ice cream in Chatham. The shop opened on Main Street in 1994 and has become a staple of downtown Chatham in the 30 years since. Scope out the family-friendly scene as you wait on the pink bench outside for your handcrafted selection. The wait can be long, but the people-watching is part of the experience.
Buffy’s is famous for its unique flavors and delicious waffle cones, as well as its thick milkshakes and Chatham Ice Cream Bars. The vintage decor is charming and evocative, transporting visitors to an idyllic (if imagined) childhood, when nothing topped a cold ice cream cone after a hot summer day. If you still haven’t satisfied your sweet tooth, head to Chatham Candy Manor right down the street.
And a Few More…
Nearby Harwich Port is also home to delicious ice cream shops, including Schoolhouse Ice Cream and Sundae School. For breakfast, pick up some pastries at Chatham Cookwear, a local bakeshop with outdoor seating and a strong selection of to-go sandwiches. As for seafood, check out the freshly-caught offerings at Mac’s Chatham Fish and Lobster (the lobster roll is a must, and you can also buy seafood from the fish market) and Impudent Oyster, as well as Pisces Coastal Kitchen in South Chatham. Lastly, the lobster nachos at the Beach House Grill have a cult following.
Where to Shop
Puritan Cape Cod
- 573 Main St, Chatham, MA 02633
Downtown Chatham is a resort-wear lover’s delight, with walkable boutiques filled with sundresses, madras shorts and nautical staples galore. Though its flagship storefront is in Hyannis, the Chatham outpost of the family-owned brand has been operating for a century, first opening its doors in 1925. Browse the racks for the latest offerings from prep classics like Barbour, Tommy Bahama and Vineyard Vines, alongside Rag & Bone and Veronica Beard. Check their event calendar for seasonal pop-ups, previewing the new season from designers such as Fair Harbor and Vince.
Mahi Gold
- 465 Main St, Chatham, MA 02633
Stroll down Main Street to the Mahi Gold flagship, a locally owned womenswear boutique. The brand is known for its unique signature prints, which often have a floral or coastal motif, among which Hydrangea Park and Vintage Bouquet are particularly popular. Though the wares are available online, some prints are in-store only and worth checking out. Peruse the Chatham Lace selection, a wrinkle-resistant fabric ideal for easy summer styling. Afterward, continue your window-shopping down Main Street to browse the designer selection at Lola Mer, another elegant boutique owned and operated by lifelong Cape Codders.
Where to Drink
Bayview Terrace
- 297 Shore Rd, Chatham, MA 02633
Grab a cocktail and reserve an Adirondack chair at Bayview Terrace to watch the most dazzling sunset in Chatham. The open-air terrace is a reliable favorite for happy hour and sundowners, so arrive early to acquire prime real estate overlooking the Atlantic and breathe in the salty air. The Terrace is only open seasonally, so capitalize on the chance to enjoy a fresh cocktail and live musical performances on a late summer afternoon. Taste the local flavors by ordering a Hot Honey Bee’s Knees, a Prohibition-style cocktail with farm-fresh honey, or the Modern Old Fashioned with Cape Cod cranberry bitters. Another spectacular sunset spot is the waterfront Beach Bar in nearby Brewster. This 32-seat open-air waterfront bar at Ocean Edge Resort is perched atop the dunes of Cape Cod Bay, with divine views of the Brewster Flats.
The Chatham Squire
- 487 Main St, Chatham, MA 02633
From sundowners to late night, the Squire in downtown Chatham is the place to visit while on the Cape for a long weekend. This Chatham institution has been the go-to watering hole for locals and tourists alike since 1968, its rustic woodwork becoming ever more adorned in the past 50 years—think Boston Red Sox memorabilia, ironic license plates from all 50 states, and antique nautical ephemera. Expect a rowdy atmosphere on Friday and Saturday nights, and plan to arrive on the earlier side to avoid the line. The vibe towards the entrance is a slightly older (saltier) crowd, while the back dance floor appeals to the post-graduate set. Trivia and karaoke nights are held throughout the week in the summertime, and live music is performed on the weekends.
And Honorable Mention to…
Wild Goose Tavern, located inside the Chatham Wayside Inn by Kate Gould Park, is also a popular haunt in town, while the Woodshed is another dive bar alternative in neighboring Brewster, replete with vintage Cape Cod decor and a stage for local musicians, and the wait time is often markedly shorter. (But no promises—get there early.)
