The only thing better than a stellar steak is one that’s served in a setting loaded with history. Those willing to venture 25 miles west along the Pike are rewarded with just such an eatery. The Oregon Club was once a speakeasy! Now, this rustic-feeling restaurant is best known for the quality of the steaks.

The Oregon Club is located at 117 Oregon Road in Ashland.
Google Maps
Back in 1922, this was the Briasco Inn, a place that appeared to be a rooming house that offered meals. However, it actually functioned as a speakeasy. The name changed in the 1930s and the business became a private club until it eventually opened to the public.
Facebook/The Oregon Club of Ashland
The interior is cozy, rustic, and a little playful.
Tripadvisor/Debi M
As you’d expect, the folks here make masterful cocktails.
Tripadvisor/CaseyfromBoston
Drink one beside the warm glow of the fire pit, before your meal.

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Start with a bowl of the restaurant’s signature spicy mushroom soup or else with the baked crab and brie bread pudding — the description alone is enough to make your mouth water.
Tripadvisor/fred200099
Moving on to the meat… "The Steak" is a 12-ounce sirloin strip steak with a crunchy char and juicy interior. Accompanied by mashed potatoes and veal demi-glace, it’ll satisfy the appetite of die-hard carnivores.
Tripadvisor/JoTeEm M
If your appetite is on the smaller side, the 8-ounce prime sirloin "Club Steak" should fit the bill.
While beef — and meat in general — is an integral part of this menu, you do have other options. Try the seared salmon, one of the Italian dishes or, if it’s comfort food you desire, there’s always meatloaf.
Tripadvisor/Rafael M
Squeeze in some dessert, if you can!
Tripadvisor/Rafael M
Reservations for this beloved eatery are recommended.
Google Maps

The Oregon Club is open for dinner every day, except for Monday, and is located at 117 Oregon Rd., Ashland, MA 01721. Have you dined at this converted speakeasy? Share your experiences in the comments.

To get the speakeasy vibe without leaving the city, you should visit Carrie Nation in Boston. Heading out to the suburbs? Then check out these other fantastic eateries while you’re there!

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