Ask The Bartender: When is the Absolute Best Time to Visit Provincetown?

best time to visit provincetown
Best time to visit Provincetown: Carnival (Photo: Michael Goff)

Is September the best time to visit Provincetown?

People often wonder which is the best month to visit Provincetown each year, the fanciful, wee, gay vacation mecca with a New England fishing-village complex. Conventional wisdom suggests you ask a local. I am here to save you a step. I will be your local, and if you’re asking me, the answer is quite easy, unequivocal, and iron-clad.

The best month to visit Provincetown is September.

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The reason is simple: September is all the good things about July and August, which are the busiest and most popular months to come to town, without any of the bad stuff.

The weather remains spectacular but is never too hot; the water tends to be just as warm if not warmer; all of the restaurants and stores and bars and clubs are still open but much less crowded; service is friendlier and faster (I am, at least). September is, by far, the best time to come visit, bar none.

Unless you’re asking me in September. If you ask me in September, I will say that June is the very best month to visit Provincetown. Now, hear me out. Remember when you were a kid and school finally let out in June and you could see your entire summer stretched out before you, the possibilities endless? June is still like that in Provincetown.

Showgirls, which starts in early June is the weekly “talent” show with its audience-chosen victor and $500 cash prize. A showcase for talents appearing that week in town, you’re as likely to witness the birth of a true drag talent as you are to see, say Jennifer Coolidge and Margaret Cho yucking it up with hosts Ryan Landry and Olive Another.

best time to visit provincetown crown
Best time to visit Provincetown: Outdoor Dining. (September)

The iconic drag performers whose shows run all summer (Dina Martina and Miss Richfield 1981 to name but two) have just begun performing again, so June is your chance to catch these legends as they hash out what works and what doesn’t before the crowds swell. 2019 marks the 20th anniversary of the Provincetown International Film Festival mid-month (you just might have breakfast next to Parker Posey or Darren Aronofsky that weekend).

best time to visit provincetown portuguese festival
Best time to visit Provincetown: Portuguese Festival (June)
best time to visit provincetown pride
Best time to visit Provincetown: Pride (June)

The Film Festival is sandwiched by the one-year-old Provincetown Pride 5/30-6/2 and the 72nd annual Blessing of the Fleet the final weekend of the month (dovetailing with the indispensable Portuguese Festival to celebrate the cultural heritage of the local fishing industry). Not to mention guesthouse and hotel rates are much more reasonable than in July and August. I tell everyone: June is, hands down, the best!

But when I say “everyone,” I just mean the people I haven’t already told that May is the best month. Really, it is! By May, it’s time to start hitting the Province Lands Bike Trail, which comprises more than seven blissful miles along the Cape Cod National Seashore. (Thanks, JFK, Senator Leverett Saltonstall, and Josephine del Deo!).

best time to visit provincetown bike
Cape Cod National Seashore (September)

It’s my favorite form of outdoor exercise and the best way to take in so many of the natural wonders that make Provincetown so special, from the spectacular sand dunes and cranberry bogs through the sun-dappled shade of Beech Forest to the breathtaking coastal scenery of Race Point and Herring Cove Beaches.

Starting the first weekend in May, you can reward yourself after your rigorous workout with some outdoor cocktails and beats during Tea Dance before treating yourself to a meal at one of the dozens of restaurants in town, just about all of which are open again, some for months.

best time to visit provincetown tea dance
Best time to visit Provincetown: Daily Summer Tea Dance

…families with children walk down the street alongside every version of every letter of the LGBTQ community

*Except for when I’m asked in May, at which point I tell people to come in July and August. That’s when all the action takes place: the most shows, the hottest weather, the largest and most colorful crowds, the freshest seafood, the busiest clubs and theme weeks, the biggest parades; there is just much more to see and do in July and August than at any other point in the year.

best time to visit provincetown harbor
Best time to visit Provincetown: Town Pier (November)

Every type of person is always welcome to come to Provincetown; in July and August, that’s when they all do. It’s amazing to be in a place where families with children walk down the street alongside every version of every letter of the LGBTQ community, from drag queens to lesbians to bears to trans people to twinks and everyone in between and outside the lines.

Provincetown wants everyone to feel that they belong here, and somehow despite our myriad differences (and to a greater extent because of them) we all do. July and August are obviously the best months to visit Provincetown for everyone.

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Best time to visit Provincetown: Fourth of July
best time to visit provincetown - carnival
Absolutely the best time to visit Provincetown: Carnival!

However, it’s when I’m in the midst of a large summer crowd that I often say the best months to come are the quieter ones. It’s difficult to top the charm of a coastal New England town that’s decked out for the holidays.

The Lobster Trap Christmas Tree comes to life the Saturday after Thanksgiving this year, with the Pilgrim Monument lighting Thanksgiving Eve, Wednesday November 27th. That weekend in town is a big one, with lots of stores offering off-season sales and many restaurants open and featuring a traditional turkey dinner among other delights.

best time to visit provincetown holly folly
The best time to visit Provincetown: Holly Folly (December)

The first weekend in December is the town’s Christmas celebration, Holly Folly, during which you can enter a one-mile Jingle Bell run. Don’t miss the official mimosa-drenched brunch afterwards (even if you don’t run). On weekends through the New Year, one of my favorite December activities are the Holiday Markets. I counted at least five Holiday markets/crafts fairs hawking mostly-local handmade wares and delicacies.

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Frosted Breakwater in the morning. (January)

I only tell people to come in the winter months if it’s clear that they want some peace and quiet and gorgeous, sublime solitude. It’s possible to go an entire day in the winter without seeing another human being at all, but this is also the time of year when you really get a sense of the community that calls Provincetown home; a few wonderful restaurants that are open nearly year round take turns being closed for a few weeks at a time, and a handful of stalwarts are actually open year round and deserve a standing ovation.

best time to visit provincetown coastguard pier
Best time to visit Provincetown: Better than average sunsets.

So not only might it be the best time to visit Provincetown, I’m finally ready to answer your proverbial question of what we do in the off season. And it should be quite apparent when I tell you that we have choices. Each week there’s not one but two local-drag-queen-hosted viewing parties of RuPaul’s Drag Race and two different trivia nights for teams at different bars, potlucks, and the annual dismantling and stowing of the Pilgrim Monument stones for the next season. See how much we all love each other?

But wait, you say, I’ve forgotten April? We keep the pleasures of that one kind of on the down-low. This month, along with May, we’re busy with a full schedule of opening parties at each major restaurant in town. They’re fun, and even if you don’t make the party, it means they’re ready to show you a good time. Ask your own bartender what’s on while you’re in town.

Best time to visit Provincetown: Halloween

Finally resolved: The very best time to visit Provincetown…

And finally, I’m putting this down at the bottom of the page in the hope that maybe you stopped reading and I kind of want to keep this secret, but fine, you got me, October is actually my favorite month in Provincetown. Bring your Halloween costume and a camera and come find out why.

Behind almost every great bar in Provincetown has stood Bob Keary at some point or another in the last 15 years.

Pictures by Michael Goff

Published at Thu, 04 Apr 2019 15:54:10 +0000