My boyfriend and I hadn’t even arrived to the hotel and I was already ooh-ing and ahh-ing over the little shops and restaurants lining Talbot Street in downtown St. Michael’s. This quaint shoretown is less than two hours from Philadelphia or Baltimore and a short ride from Washington D.C which makes it the perfect place to get away for a weekend.The incredible Inn at Perry Cabin is located an easy 10 minute walk outside of charming downtown St. Michaels. Its inlaid brick and tree lined entrance captivate you the second you arrive on property. The endearing manor house sits along the water boasting beautiful water and garden views in the summer and stunning autumnal foliage which we were fortunate enough to witness.

We checked-in to a Deluxe Garden View Room that had just the right touch of “19th-century elegance”. The room was beautifully appointed with a large 4-post mahogany bed, immense picture windows, allowing for copious amounts of sunlight, and an incredible deck that became a perfect spot for drinking espresso in the morning and appreciating the natural surroundings. I would have been more than happy to stay in the room for the entire weekend but we were on a mission to explore what this Eastern shore town had to offer!
Our first evening in St. Michaels, we enjoyed a casual dinner at the downtown hotspot Ava’s Pizzeria & Wine Bar. Known for their brick oven pizza and wide array of beer on tap, they definitely did not disappoint. We sat down and what seemed like a slow night quickly turned into a busy and buzzing Friday!

We ended the evening cozied up by the fire on a plush leather couch at the Inn’s main bar, Purser’s Pub. While sipping my cocktail and taking in the Pub’s old-world charm, I could easily imagine soaking in summer sun in the adjacent garden courtyard. Saturday morning began as every Saturday should. We woke not to the sound of an alarm but to the light filtering into the room. The smell of fresh espresso brewing and the promise of breakfast were the only things pushing me out of that dreamy king bed.

The main restaurant at The Inn at Perry Cabin, Stars, has floor to ceiling windows facing the bay. Although known as an enticing dinner spot, enjoying breakfast or lunch in Stars seemed just as satisfying. Sipping on a mimosa with the sparking blue Chesapeake waters in the background painted the perfect backdrop for an amazing meal.
We spent the remainder of the day riding bikes along the main street passing, little boutiques and locally owned restaurants with flower boxes on the windows and inviting store fronts. The sun was shining and air was crisp so we were cut off the main street and explored the back roads as well. Along the way, we passed countless colonial brick homes with street signs that took you back to the 1800’s. We then stumbled upon a rum distillery that was calling our names.
Lyon Distillery was founded in 2012 and is a micro distillery focused on creating distinctly American spirits. Every spirit passes through the hands, and discerning palates, of co-founders Ben Lyon & Jaime Windon who we were able to meet on a tour of the distillery. Clearly passionate and invested in the distilling business, they took us through the whole process. This was naturally followed up with a complimentary tasting of their products – delicious, local, and crafted by great people, their mission is easy to support.

After a couple tastings of rum, vodka, and whiskey it was best to make our way back to the hotel. We ended the evening with a stroll along sapphire waters and passed people sitting on Adirondack chairs in the grass, sipping their wine and snacking on small bites. We took a pit stop and cozied up at the fire pits to warm up as the sun was starting to set.
Our last morning, we decided to enjoy our breakfast outside on the deck. Our exquisite feast arrived promptly and the server was quick to assist us in setting up on the deck. We delighted in our breakfast and the beauty of the changing leaves and sounds of boats bobbing by the dock.
We reluctantly packed our bags and checked-out. We were heartbroken to say goodbye to our delightful room and marvelous deck. In a short 3 days we’d become so accustomed to relaxed pace of The Inn at Perry Cabin. On our way out of St. Michaels we stopped for a bite at Awful Arthurs. We kept nice and cozy next to a fire pit as we sipped Bloody Marys and enjoyed of course, Maryland Crab Chowder!

By booking your weekend getaway at The Inn at Perry Cabin with Avenue Two Travel you will enjoy the following amenities:

  • Upgrade on arrival, subject to availability
  • Daily Continental breakfast served in the restaurant for up to 2 in-room guests
  • $100 USD equivalent Hotel & Resort credit to be utilized during stay
  • Early check-in/late check-out, subject to availability
  • Complimentary Wi-Fi

Activities Offered at The Inn at Perry Cabin:

  • Open-Air Movie Nights
  • Kayaking
  • Sailing and Boating
  • Fishing
  • Oyster catching
  • Wine Tastings