Our pub crawl started with oysters and ended with singing along to “Sweet Caroline” in a building where George Washington reportedly slept.

Along the way, I was introduced to a 9-pound copper flamingo.

It was the kind of evening that felt unique to Annapolis. My wife and I agreed to host four people on a stroll across four of the city’s watering holes to benefit a charity we support. The rules were one drink in each bar, and you had to eat.

You could do this at any time of year, of course. But daylight saving time ends Nov. 3, and starting a night on the town after dark makes it feel less debauched, or maybe it’s just a different variety of pink elephant. Or flamingo, your choice of hallucination.

Here’s what we tried.

Sailor Oyster Bar, 196 West St. 6:10 p.m.: Arguably the hippest bar in Annapolis and the hardest to get into some days. SOB reopened earlier this year after a calamitous fire in 2022, with its menu of craft cocktails, interesting beers, hard-to-find oyster varieties and exotic tinned fish. No reservations, so it took about 40 minutes to find a table for six. Not bad, and some nights the place is so packed you have to wait for two spaces at the bar. And people do it. Timber Pizza Co. is next door if you can’t wait.

Harold Black, 236 Main St. 7:35 p.m. The walk down West Street around Church Circle to Main took 10 minutes, but we spent another 15 minutes pursuing Gallery 57 West, a collective of local artists. The entrance to Harold Black is through Acqua Al 2, a popular Italian restaurant. Head downstairs to the very dark basement and you’ll find brick walls, exposed pipes, two rooms of tables, booths and a large bar. I needed my phone flashlight to read the menu, but the espresso martini and 50-50 old fashioned came highly recommended. It’s the only place in town where I’ve found Nastro Azzurro.

Pearl Annapolis, 26 Market Space. 8:15 p.m. If you’re out on a crawl, you have to be ready to improvise. Our planned destination, Parley Room on State Circle, was closed for a private event. So we strolled past its deck overlooking the statue of the Baron de Kalb and the Maryland State House on a six-minute walk to City Dock. The Flamingle Punch Bowl at this Pacific Island-inspired restaurant and tiki bar made it the surprise of the evening. Absolut Elyx, Velvet Falernum, Lillet Rouge, prosecco, passion fruit and lime served in a 9-pound copper flamingo — copper stills used to make the wheat vodka set up the kitschy marketing idea. Divided among us, it worked.

Middleton Tavern, 2 Market Space. 9:15 p.m. Middleton Tavern was around before the revolution, and while the building is the original structure where George Washington spent some nights, the family-run restaurant and bar has been around for decades. That makes it one of the longest-standing businesses in downtown Annapolis. A one-minute walk for us, we headed upstairs to catch Donald Wolcott at the corner piano playing sing-along hits like Neil Diamond’s “Sweet Caroline.”

After my share of the Flamingle, this seemed like a perfect cap of the evening. We were home by 11 p.m.

If you opt to do this sort of thing, be safe. Know your limits, and have a plan for getting home if you drink too much.

Here are some things to do in the next week.

Haunted options

Friday-Sunday

Take the evening hayride or try the haunted barn this weekend at the Anne Arundel County Fairgrounds. Halloween Happening runs from 7 p.m. to 10 p.m. Friday and Saturday, 7 p.m. to 9 p.m. Sunday. $15 plus taxes and fees.

En pointe

7:30 p.m. Friday

Ballet Theatre of Maryland presents “Napoli,” the story of a fisherman named Gennaro who hopes to marry his beloved Teresina, at Maryland Hall. The performance repeats at 1 p.m. Saturday and 2 p.m. Sunday. Adult general admission tickets are $62.35, with cheaper pricing for seniors, active military, students and children.

Onstage

8 p.m. Friday

Colonial Players presents “The Winslow Boy,” a 1948 British play about schools, injustice and consequences for a student and his family. The play continues at 8 p.m. on Thursdays, Fridays, and Saturdays, with 2 p.m. Sunday matinees through Nov. 16. General admission tickets are $26.

Trick or 45-foot response boat

10 a.m. to 4 p.m. Saturday

Halloween is Thursday, Oct. 31 and trick-or-treaters will be out. But you can head to one of many scheduled “trunk or treat” events. Then, there is the open house at the Annapolis Coast Guard station.

The Halloween-themed event for kids coincides with the station’s yearly open house, which includes tours of the station at 11 a.m., 1 p.m. and 3 p.m. The station, home to 45-foot response boats and other equipment, is one of several on the Chesapeake Bay hosting the events. Adults must provide a valid ID. Free.

Feliz día de los muertos

3 p.m. to 8 p.m. Saturday

The city of Annapolis will host its Día de los Muertos Festival at Maryland Hall. Costumes, sugar skull makeup, live music and more are planned. Free.

What are those things?

Through early November

If you drive West Street, you may have noticed some odd figures standing stiffly by the side of the road. They’re part of Scarecrow Stroll, hoisted up by teams, schools and businesses across Anne Arundel County. You can vote for the best. Free.