At 9 PM, for the first time in my life, my mom and I are sitting at a bar counter together. We listened to a live performance by a pianist and vocalist who was accompanied by a musical performer in the crowd. We noticed the performer’s increasing aggravation at this unwelcome accompanist. We drank our mocktails and laughed away until it was time to line up for the Cabaret show.
My mom (50) and I (26) have been coming to P-Town every September for the last three years.
She is normally asleep by 7 PM but tonight, she agreed to stay out with me to see a live show because we were walking distance to our Guest House, and the Drag Karaoke event we wanted to go to was done for the season.
We normally indulge in the popular activities of whale watching, sitting on the beach, and eating at outdoor eateries. But this time it rained, canceling all of our scheduled activities, and causing us to be creative and discover the hidden gems of Provincetown.
Whether it’s your first time or your 100th time, there’s a special charm about P-town that keeps you wanting to stay and linger. Use this guide to help you explore Provincetown rain or shine.
Jump To:
- Things To Do – Indoor & Rainy/Cold Day Activities
- Things to Do – Warm Weather Outdoor Activities
- Restaurants
- Accommodations
- FAQ
Things To Do
Indoor Cold Rainy Day Activities
Drag Karaoke & Brunch
Many restaurants offer drag brunch and/or karaoke. Governor Bradford is known for their nightly Drag Karaoke, make sure to check with the restaurant if the season is over or not.
The Crown & Anchor has a popular drag brunch that I haven’t tried yet because whenever I remember to book a reservation, they’re full – so book ahead of time!
Explore the local shops
There is a diverse selection of shops to check out in P-Town. Here are some of my recommendations:
- Womenscrafts (for women’s art, literature, and clothing)
- Respoke (products made from Hérmes scarves)
- Birdie Silkscreen (for classic screen-printed clothing)
- House of Monty’s (for a unique selection of home goods)
- Tim’s Used Books (get lost in this bookstore!)
- Whalers Wharf (center full of shops, galleries, restaurants, and public restrooms!)
Watch a Show & Listen to Live Music
We went to the Post Office Café and Cabaret on our latest trip. Pre-show, we listened to live music and ordered mocktails in the cafe. Then headed upstairs to the cabaret for The Devil Wears Payless, a spoof of The Devil Wears Prada. We laughed so hard. Apparently, Meryl Streep heard about their production.
I truly can’t believe this was the first time that we experienced a cabaret show in Provincetown. The production and talent are exceptional. I highly recommend finding a live show to watch.
Visit Art Galleries & Museums
There are tons of art galleries to bounce around on the main street and inside Whalers Wharf. For museums, check out the Provincetown Art Association Museum, and the Pilgrim Monument and Provincetown Museum.
Check out the Provincetown Public Library
If you find yourself stuck indoors, be sure to check out the local library. Not only is it beautiful but they may have some events happening. We happened to be there during the Provincetown Library annual Book Festival with literary events, author readings, and talks.
Warm Weather Outdoor Activities
Whale Watching
The Dolphin Fleet is the best whale-watching tour that I’ve been on. The ship is large and has an indoor area. Some tour companies use sailboats so there is no overhead from the rain or cold.
The captain and shipmates gave us plenty of time to spot and watch the whales breach. They also told us to watch for the dolphins playing in the waves from the boat.
The Ponds
I learned from guests at the Revere Guest House that swimming in the ponds of Wellfleet is better than the coast because there are no sharks and they’re very clean. Gull Pond, Long Pond, and Great Pond to name a few.
Restaurants
Front Street
Front Street Fine Dining will transport you to old-school Italy with classical music, brick walls, and upscale Italian fare. I ordered the veal parmigiana and my mom ordered the salmon special. For dessert, we split the bread pudding.
Jimmy’s Hideaway
Jimmy’s Hideaway is highly recommended by locals and tourists alike. It’s in a very small, intimate setting so be sure to book a reservation.
Governor Bradford Restaurant
Governor Bradford has an amazing secret. When you walk in, it looks like a typical local bar but they have an exquisite sushi and sashimi menu along with other bar food items. They have nightly entertainment and Drag Karaoke during the busy season.
Pepe’s Wharf Restaurant
Pepe’s Wharf is a classic seaside restaurant that you must visit to eat and take in bay views. I ordered a veggie wrap and a spicy margarita and my mom ordered a blackened cod sandwich and a piña colada.
The food was so good that the server commented on how my posture relaxed after eating.
Lobster Pot
Lobster Pot is a laid-back restaurant for fresh lobster and seafood with bay views. The lobster roll is not to miss!
The Canteen
I loved The Canteen! We ate brunch on their beach-side picnic tables.
Kohi Coffee
For a quick coffee or a moment to take out your laptop, come to Kohi Coffee. There are two locations. The 376 Commercial Street location is where you will find seating, the other location is only for getting drinks to go.
Accommodations
The Revere Guest House
The Revere Guest House is a cozy bed & breakfast centrally located in downtown Provincetown.
I absolutely loved my stay here – especially since we were stuck in the rain. The location is perfect for walking to many of the restaurants and activities around Main St. Provincetown. We didn’t need to use our car at all.
One of my favorite parts was the common area which had a gorgeous fireplace, comfy seating, and a selection of all-day snacks and drinks. We also enjoyed a full breakfast every morning. Naturally, all of the guests convened in the common room every morning and night and we shared about our plans and how the day went.
My mom and I stayed in Chatham Room 8 which had a gorgeous balcony overlooking the bay. The bathroom had a jacuzzi bathtub and they provided bath salts. Obviously, I indulged in a bath. The room felt luxurious and was completely renovated.
I’d return here in a heartbeat!
Sandcastle Resort & Club
View from the resort and beyond the marsh is the private beach.
The Sandcastle Resort & Club is a beachfront property located about two miles away from downtown Provincetown.
The main benefit of staying here is that you will have direct access to a private beach. But for me, that is the only reason to stay here. Otherwise, it’s far from the downtown area and the amenities and rooms need a major update. Ensure to book an oceanfront room to make the stay worth it.
FAQ – Frequently Asked Questions
When is the best time to go to Provincetown?
The best time is the first or second week of September because the crowds from earlier in the summer are gone but everything is still open. My mom and I went towards the end of September this year and some of the restaurants closed for the season and some entertainment stopped.
Can you go to Provincetown if you’re straight?
Totally! My mom and I take an annual mother-daughter trip here. You will be surrounded by positive and supportive people, places, signs, and stores. It is important to be an ally here because it is a safe space for the LGBTQ+ community, where people can feel free and open to be themselves. If you’re not okay with that then P-town may not be the place for you.
Is a trip to Provincetown worth it?
Yes, absolutely! Provincetown is likely one of the most active towns on Cape Cod. There are tons of activities and restaurants to check out.
How many days to spend in Provincetown?
I’d recommend 3-4 days to stay in Provincetown. My mom and I always go on an extended weekend trip. Weather permitting, one day you can go out on a whale watching tour, the next day you can spend exploring the downtown area, and the following days you can venture to some of the nearby ponds and beaches.
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