Weekend in ... Provincetown

Perched at the tip of Cape Cod – or at the end of the world, as locals like to say – Provincetown is a quirky beach community favoured by artists, drag queens, LGBT people, heterosexual families from the suburbs and oddballs on the run. Provincetown combines small-town charm with big-city spunk, nestled among miles of peaceful dunes and seashore.

If you want solitude, come in the winter when hardly anyone is here – or anything is open. But if you’re after warm weather and high-season theatrics, arrive in July, August or early September. Be careful about what summer week you choose. Many have a theme, and your Provincetown experience will differ whether you’re here for “Family Week,” “Girl Splash” or “Bear Week”.

Friday
4pm 1 Oysters and Celebrities Rent a bike from one of the handful of rental shops in town – if you arrive by ferry, the closest is Arnold's Bikes – and head west for about a mile on Commercial Street, the town's main drag. Try not to crash into any famous writers on the way – John Waters, Tony Kushner, Andrew Sullivan and Michael Cunningham are generally in residence during the summer. (Before your visit consider reading Cunningham's Land's End: A Walk in Provincetown, a celebration of the town and the best introduction to the area.) Stop at the Red Inn and savour $1.25 (€0.93) shrimp and Wellfleet oysters or cocktails on the deck with views of the harbour and the Long Point Lighthouse. The Red Inn is also one of the town's best upscale dinner spots.

5pm 2 Break for the Breakwater Take a left out of the Red Inn and bike to the other side of the roundabout at the end of Commercial Street. You’ll see the breakwater, a mile-long stretch of mammoth granite blocks that leads to a mostly deserted portion of Herring Cove Beach. Two warnings: the breakwater is longer than it appears and its rocks are better traversed sober. Any trip to Provincetown though, without at least a partial trek along those rocks, is probably incomplete. If it’s high tide, go for a swim in the lagoon that forms along the breakwater. If it’s low tide, walk across the harbour floor to the beach.

7pm 3 Strolling for Art Painters love Provincetown for its distinctive vistas and breathtaking light. On Friday nights you can admire the work of celebrated Cape Cod artists – including Anne Packard and John Dowd – in dozens of galleries that stay open late. (Many offer wine and cheese.) Concentrate your efforts in the town’s East End and be sure to visit the Albert Merola Gallery, William-Scott Gallery, Schoolhouse Gallery and Julie Heller Gallery East. Also drop by the 100-year-old Provincetown Art Association and Museum, which is free on Friday nights and features exhibitions and workshops year-round.

8.30pm 4 Drag Queens and Quartets There is never a shortage of entertainment here, from street performers to big-name nightclub acts. Commercial Street is rich with drag queens hawking their shows (sometimes perilously on bicycles and mopeds), and one of the local favourites is the offbeat and inimitable Dina Martina (Crown & Anchor, $25/€18.67), who has been performing here every summer for 10 years. Well-Strung – a talented quartet of men who sing and play string instruments – got its start in Provincetown and brilliantly fuses pop and classical music from Madonna to Beethoven (the Art House; tickets, $30/€22.40).

10pm 5 Toast the Town For a late-night meal or drink, head to the Nor’East Beer Garden’s outside tables. Order the beer-battered fish and chips or a dozen oysters ($24/€17.92) and choose from a wide array of local beers. If you would rather drink wine, go west on Commercial Street to Joon Bar and Kitchen, an outstanding restaurant and wine bar that serves food until 10pm and drinks until 1am. Don’t miss Joon’s fried olives ($9/€6.72), roasted halibut ($20/€14.94) and fries with foie gras aioli ($9/€6.72).

Saturday
10am 6 Climbing Through History Grab a delicious breakfast sandwich (from $4.25/€3.17) or blueberry muffin ($3/€2.24) at Connie's Bakery and pick a spot to enjoy it a few feet away on the deck at Aqua Bar at the rear of the Aquarium Mall. (You can't beat the harbour views.) After breakfast, head toward the tallest structure in town – the 252ft tall Pilgrim Monument. Built between 1907 and 1910, the tower commemorates the arrival of the Mayflower pilgrims in Provincetown. (The pilgrims hung around for a few weeks before deciding that this was no place for a permanent settlement.) The monument is the country's tallest all-granite structure and offers stunning sights of the town, Cape Cod and, if you're lucky, Boston's skyline. At the base of the monument is the Provincetown Museum, which chronicles the maritime history of the town.

1pm 7 Relish the Canteen Provincetown’s best casual lunch spot is the Canteen, a charming Cape Cod-style dining spot in the heart of town. There are a few tables inside, another pair on the street (perfect for people-watching) and a long communal table in the backyard near the beach. Don’t leave the Canteen without trying the cod banh mi ($9.99/€7.46), pulled pork tacos ($13.95/€10.42) and crispy brussels sprouts in fish sauce ($7.99/€5.97). If you want something you can easily take to the beach, walk or bike to Relish in the West End and try any of its delicious sandwiches (all for under $9/€6.72).

2pm 8 A Beach for Everyone Provincetown’s most visited beach is Herring Cove, which is only a short bike ride away and has gentle surf and views of the setting sun. Herring Cove is unofficially divided into sections: the closest to the car park is where you’ll find families, many with small children. If you walk south (or to the left when facing the water), you will cross into an area favoured by lesbians, followed by one favoured by gay men, followed by one favoured by naked gay men. Prefer your parcel of sand devoid of sexual identity politics? Then bike the Province Lands Bike Trail – or take a shuttle from MacMillan Pier to Race Point, a prettier beach two miles from town.

5pm 9 Rowdy Little Tea Party If Commercial Street seems quieter between 5pm and 7pm, that’s because a good portion of the town’s visitors are at Tea Dance at the Boatslip Resort. There is no actual tea served at this deck-side party overlooking the harbour, but there is a $10 (€7.47) Planter’s Punch designed to get you drunk before dinner. For a quieter alternative, go shopping. In the West End, be sure to visit Loveland, where you’ll find eclectic and bohemian handcrafted furniture, ceramics and clothing curated by the shop owner, Josh Patner.

8pm 10 Dinner Scene If you’re hungry for old-school Provincetown, head to the restaurant called Front Street, a town favourite with some of the best Italian food around. You can’t go wrong with the carbonara con pappardelle ($21.95/€16.39) or the braised beef and short-rib ravioli ($23.95/€17.89). For a tasty alternative off Commercial Street, dine at Backstreet, a two-storey restaurant with both indoor and outdoor seating. Don’t miss the chef Raul Garcia’s hand-ground grits ($9/€6.72), blue corn calamari ($12/€8.96) and Brazilian fish moqueca ($26/€19.42).

11pm 11 Cats and Cocktails There are many bars and clubs in town, with most catering to the LGBT community. Start your evening at Shipwreck Lounge, where couches and a fireplace (not to mention the two friendly house cats) make you feel as if you’re in someone’s upscale living room. Out back, there’s a fire pit and lounge seating. If you’re in the mood to dance, skip over to A-House. Built in 1798 (and seemingly never renovated), the building now houses a dance floor and patio that’s busy after 11.30pm on summer nights. You’ll want to start your dancing early, though. Bars here close at 1am, after which a spirited crowd routinely continues the party in front of Spiritus Pizza on Commercial Street.

Sunday
11am 12 Romancing the Brunch There are several good breakfast spots in town, including Devon's (in the East End) and its sister location, Devon's Deep Sea Dive (in the West End). Try the pancakes with fresh strawberries ($11/€8.22) or breakfast burrito with home fries ($14/€10.46). The East End location is perfect for a romantic meal, especially if you score a table on the covered front patio.

1pm 13 Whale of a Good Time You can often spot seals near the shoreline while sunning at Herring Cove or Race Point beaches, but if you’re after a bigger catch, try a three-plus hour Whale Watching Tour courtesy of Dolphin Fleet ($46/€34.35 for adults).

The details:

Arnold’s Bikes, 329 Commercial Street; 508-487 0844

The Red Inn, theredinn.com

Albert Merola Gallery, artsy.net/ albert-merola-gallery

William-Scott Gallery, williamscottgallery.com

Schoolhouse Gallery, galleryschoolhouse.com

Julie Heller Gallery East, juliehellergallery.com

Provincetown Art Association and Museum, paam.org

Crown & Anchor, onlyatthecrown.com

The Art House, ptownarthouse.com

Nor’East Beer Garden, noreastbeergarden.com

Joon Bar and Kitchen, joonbarandkitchen.com

Connie’s Bakery, conniesbakery.com

Aqua Bar, aquabarptown.com

Pilgrim Monument, pilgrim-monument.org

The Canteen, thecanteenptown.com

Relish, ptownrelish. com

Herring Cove Beach, Province Lands Road

Boatslip Resort, boatslipresort.com

Loveland, lovelandprovincetown.com

Front Street, frontstreetrestaurant.com

Backstreet, backstreetptown.com

Shipwreck Lounge, ptownlounge.com

A-House, ahouse.com

Spiritus Pizza, spirituspizza.com

Devon’s, devons.org

Dolphin Fleet, whalewatch.com

© 2014 The New York Times, distributed by The New York Times Syndicate