A Boozy Guide to Cape Cod (and Thereabouts)

“Thus the great civilizer sends out its emissaries, sooner or later, to every sandy cape and light-house of the New World which the census-taker visits, and summons the savage there to surrender.”
– Henry David Thoreau, Cape Cod

There’s something about the last days of August that bring me low. Sure, it’s oppressively hot and humid, but you know, deep down, that in a few months you’ll miss it.

So, in an attempt to overcome the August doldrums, I struck north for the idyllic Yankee beaches and towns of Cape Cod. The climate gods did not let me down – perfect weather made for many a relaxing morning spent on the beach, long strolls through quaint coastal towns, and outdoor drinking. Lots of outdoor drinking.


Determined to pierce Cape Cod’s genteel veneer and get to its hard drinking underbelly, I conducted an extensive reconnaissance of the peninsula’s finest watering holes. To bring order to chaos and help the thirsty reader, I whimsically categorized the 13 spots I visited. So, without further ado:

Bring your Lacoste shirts 

I wouldn’t call Cape Cod pretentious, but let’s face it – there’s lots of yachts around. And big houses. So there’s going to be a good list of high-class bars where you can show off your new blue blazer and fancy boat shoes.

First up, Mahoney’s Atlantic Bar and Grille in the too-cute little town of Orleans. A classy joint where you’ll meet plenty of friendly boaters and well-to-do locals, Mahoney’s offers a good variety of beer options and classic cocktails in a relaxed and refined setting. Mahoney’s gleaming bar and furnishings provide a good setting for a business meeting or dinner with your parents after a long day of sightseeing. When you’re done there, head west for some pasta and simple drinks at Celestino’s. The Italian eatery is cozy and lovably local, with a comfortable bar and excellent, uber-friendly service.





If you’re looking for something spicier, take a trip to Anejo’s Mexican Bistro in Falmouth, a town which could not be more Cape Cod-ish if it tried. Anejo’s offers some interesting tequila mixes and doesn’t skimp on the heat; while I was there, they were preparing some pepper-ish syrups that made my eyes water. A dark bar and eye-catching Mexican artwork makes for a classy affair. If whiskey is more your speed, it’s hard to top Oak and Ember, an upscale eatery that offers an extensive arsenal of spirits and cocktails for those with discerning tastes. This is a serious drinking spot, perfect for a long Saturday evening with people who like to test their palettes.



Another well-bred bar worth stopping in at is the Belfry Inn and their cocktail lounge, CW’s. Smack dab in the middle of gorgeous small-town Sandwich, the Belfry is built in an old church and nearby mansion, the perfect setting to sip some wine or heartier fare. I learned that a healthy number of Europeans stay and work at the Belfry during the summer, so it’s a good locale for trans-Atlantic exchanges, which are are even more interesting with gin. In terms of seaside elegance, however, it’s hard to top the modernist Harbor Lounge in scenic and lively Provincetown. Furnished with chic leather couches and featuring its own water walk, this is the perfect spot for cocktail-soaked frivolity or early evening drinks watching the sun go down.



Talk to the locals about the Saux

Maybe it was the salt in the air and fishing boats at sea, but I felt compelled to visit some of the more blue-collar, local bars the anchor so many Cape Cod towns. One of the nicest was the Black Cat Tavern in Hyanniswhich is beautifully decorated with artifacts of the towns proud nautical tradition. Situated across the street from the endless docks of Hyannis harbor and well-stocked with local brews, the Cat is the perfect spot to relax and make up stories about the bass you caught that morning. For an even grittier but no less fun spot, head east to Sundancer’s. This tucked-away harbor side bar is no frills but oh so much fun, with cheap beer, colorful locals, and dancing. And no one dances as well as tipsy Cape residents – trust me.



If you’re looking for a real earthy Cape Cod experience, however, you’d be hard pressed to beat the Beachcomber. Challenging to get to on an isolated part of the peninsula, this beachside bar is windswept, sandy, and Cape Cod as hell. After pounding cheap beers or simple tropical drinks in the company of the local salts, you’ll be extending your As and learning how to tie knots in no time.


Bring your suntan lotion

Honestly, even though I love dark bars, it’s hard to justify spending time indoors when the sun is shining and the breeze blowing. Ah, I have a solution – outdoor bars! Luckily, many a businessman and woman has figured out how profitable such an endeavors can be, so you’ll have plenty of opportunities to enjoy Mother Nature and her natural companion, booze.

There’s no better outdoor party spot than the Chart Room, a dockside bar and grille that gives you two options. Drink through an extensive cocktail or bar list inside an old school sailor’s bar, or drink outside along the water. Can’t go wrong! Throw in tons of local, seasoned day drinkers and you have yourself a Cape Cod party. If you’re looking for a more sedate outdoor spot, visit Truro Vineyards and South Hollow Spirits. Set amongst the beachside grapes and featuring a peaceful courtyard, you can do group tastings or buy a glass to relax with. I’d also recommend giving their gin a try, it had a very unique peppery burn I hadn’t tasted before.

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One benefit of Cape Cod is its proximity to Newport, one of my favorite towns in all of New England. Built by Gilded Age hands, the seashore town is elegant and timeless. Few spots evoke the character of the town more than the Castle Hill Inn, an ornate and stately manor that features breathtaking views of the Atlantic. You can enjoy a full and peppy cocktail list at the outdoor bar or on a comfortable lawn chair. A must see spot if you love to drink with the sea breeze in your face. You won’t get quite the same views at 42 North in Plymouth, but you will meet friendly locals and awesome bartenders. A good end of the day spot.





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