History and a Host of Activities at the Berkshires’ Red Lion Inn

This hotel in Stockbridge, Massachusetts has more of a homey than a hotel feel

The Red Lion Inn is clearly dedicated to providing experiences and the highest level of guest services.

The biggest surprise about the Red Lion Inn in Stockbridge, Massachusetts is probably the fact that I had never heard of it prior to my visit. 

After all, not only is it a prestigious and historic inn that opened in 1773, but it has hosted five U.S. presidents (Cleveland, McKinley, Coolidge, and both Roosevelts). Currently on the up-and-up thanks to a laundry list of additions, numerous family members and friends — from Upstate NY to my home base of Portland, Maine — told me they had heard of, or even stayed at, the Red Lion Inn.

Located on Route 7 just a few minutes off of I-90, the Red Lion was once a small tavern that attracted travelers making the journey between Boston and Albany. Today, it’s one of the most popular lodging options in the Berkshires, a mountainous region of Western Massachusetts known for outdoor activities, top-notch leaf-peeping, fine dining, and local farm-to-table everything.


Rebecca Lanae

Although the main inn contains a wealth of rooms (82, to be exact), it definitely doesn’t have a “hotel feel.” The Red Lion Inn doesn’t identify as a hotel by name either and eschews terms like “standard”, “deluxe”, or “superior” when it comes to room types, although it does house numerous suites.

“Each of our rooms is special and tells its own unique story,” the inn’s website proudly states.

Like the homey lobby, corridors, and dining rooms, the guest rooms are adorned with traditional charm and antique furnishings, many of which came courtesy of Mrs. Charles H. Plumb, a collector who purchased the Inn with her husband back in 1873. These fixtures have seen countless visitors and survived a lot in the past 145 years, including a fire that destroyed the entire main building in 1896.

Still, the inn and its rooms are peppered with modern features like widespread WiFi, flat-screen TVs, and alarm clocks, as well as comforts like luxurious linens, complementary toiletries, and plush bathrobes.

In addition to the main inn, the property also features several separate guest houses, including a turn-of-the-twentieth-century firehouse immortalized in Norman Rockwell’s painting “The New American LaFrance is Here” and a private house on the grounds of the nearby Chesterwood estate (the former home of sculptor Daniel Chester French).

On our trip, we stayed in the Maple Glen, a 17-room guest house located just behind the main inn. The recently renovated Maple Glen has a similar retro vibe (while still offering modern perks like Bluetooth speaker-equipped alarm clocks, heated bathroom floors, rain shower heads, mini bars, and Keurig machines) but with more of a bed and breakfast feel. The B&B atmosphere isn’t due to intrusive hosts or an army of roaming cats, but more so because the Glen feels like a home, complete with a large porch and a indoor common area that offers a shared kitchen, a large dining room table, furniture for relaxing, and a fireplace that gets plenty of use in the colder months. (For the record, cat lovers will be pleased to know that while the Red Lion Inn isn’t full of a herd of cats, it does have a feline mascot: a kitty named Norman who lives in the main inn.)


Rebecca Lanae

Pull Up A Chair Anywhere

We didn’t get to use the dining room table because the Red Lion offers numerous on-property dining options. For casual fare, there’s the Lion’s Den pub in the basement, the rustic and family friendly Widow Bingham’s Tavern (dinner only), and seasonal al fresco dining in the courtyard, as well as the more upscale main dining room, which is open for breakfast, lunch, and dinner daily.

The Red Lion wants to make sure they take care of the tough decisions during your vacation, but there is one they can’t avoid and it comes at the start of the day. Each morning, we were greeted with a difficult choice in the form of the dining room’s breakfast menu. Because let’s be frank: who can pick just one item when the options include banana nut French toast (with maple-glazed bananas and walnuts), grass-fed corned beef hash and poached eggs, traditional or smoked salmon Eggs Benedict, shiitake mushroom hash, or made-to-order omelets and breakfast sandwiches?

Lunch offerings include a variety of soups, salads, sandwiches, and entrees like calamari, beer-battered haddock, and a signature chicken pot pie, while dinner centers on a veritable haul of seafood (scallops, swordfish, salmon, and mussels) as well as Berkshire pork loin and prime rib for the ocean-averse.

We were lucky enough to sample a sneak peek of the Red Lion Inn’s summer menu, which will boast chicken liver pâté, smoked trout, and strawberry and basil burrata appetizers; chilled sweet pea soup with spicy shrimp; house-made cavatelli with asparagus and local morel mushrooms; pan-seared scallops with grilled vegetable caponata and tomato vinaigrette; and grilled filet of beef as a main course. There were also several dessert options but I’m pretty sure I blacked out due to food-fueled euphoria by that point, and the details escape me. (And the wonderful wine pairings with each course likely had a hand in this too.)

Don’t Forget the Memories

The most interesting part of the current Red Lion Inn, however, might have been the fact that General Manager Robert “Mick” Mickey didn’t spent a lot of time discussing the inn’s history, its decor, or its food (short of praising the farm-to-table aspect and describing the upcoming menu) during a cocktail hour hangout on the main inn’s expansive front porch. Instead, he harped on the experiences the inn offers.

Although he never explicitly stated this, this tactic is likely directed at the inn’s younger generations of visitors, who have made it clear they value memories more than materials things.

In other words, while older generations generally saw hotels simply as rooms, beds, furniture, and decorations, younger travelers seek something more. In fact, you could almost turn Mick’s talk into a drinking game if you took a sip every time he said the word “experience” when talking about new developments at the hotel. We didn’t play, however, because we would have downed our cherry lime gimlets (made with local, award-winning Greylock gin from Berkshire Mountain Distillers) a bit too quickly.

The longtime hotelier rattled off a number of new or continuing events and offers at the Red Lion Inn, including live music in the Lion’s Den at 8 p.m. every night, occasional “Den Sessions” that feature hand-picked local musicians, and the possibility of moving some music into the picturesque courtyard, too, which already holds cookouts on Fridays during the summer months.

The aforementioned enormous front porch will also host numerous events throughout the summer, including various wine tastings on the second and last Wednesdays of June, July, and August that revolve around whites, rosés, chillable reds, and ciders, as well as cocktails like gin and tonics.

As additional entertainment, Mick said the porch will continue to be the scene of theater performances courtesy of local thespians who showcase snippets of their productions while mingling among the inn’s guests.


Rebecca Lanae

Even if the guest’s desired activities take place off-site, the inn is willing to help out. Mick is pioneering a new shuttle service that will transport lodgers around town to various events, including shows at the historic nearby Tanglewood music venue, which hosts touring musicians and is also the summer home of the Boston Symphony Orchestra.

By the end of the visit, it was obvious that the Red Lion Inn, after nearly 250 years, still has plenty to offer its guests, and the list continues to grow with each passing season. In addition to being a luxurious but homey place to rest one’s head, it’s also a place to eat fine, farm-to-table food; sip local brews, wines, and spirits; and enjoy entertainment and activities both on and off the property.

The Red Lion Inn is clearly dedicated to providing experiences and the highest level of guest services, no matter what it takes. For example, if the shuttle service is a hit (and early reservations indicate it will be), Robert Mickey proclaimed he will order a larger shuttle, or a bus, or whatever sized vehicle it takes to meet the demand.

“I’ll shuttle them around myself, if I have to,” Mick said with a smile.

And with the Red Lion’s sparkling track record, we believe him.

Related Stories
15 Things Your Hotel Concierge Won’t Tell YouYou Can Literally Have Breakfast With a Giraffe at This Kenyan HotelThe 30 Best Hotel Pools in America

Meals and accommodations in the above review were provided at no cost to the contributor.