Midnight Madness in St. Michaels

Only 16 days until St. Michaels’ biggest shopping day of the year! Are you ready for the 9th annual Midnight Madness??


Saturday, December 4th, St. Michaels will host its annual shopping extravaganza. The shops and boutiques throughout the town will keep their doors open until midnight and will be offering unbelievable savings that you will not want to miss!

Refreshments and snacks will be served and Carolers will be walking the streets to serenade all shoppers. Every shopper will receive a ticket to win great prizes with each $15.00 purchase that is made. The drawing for the prizes will take place promptly at 11:30 pm in London’s parking lot—between Railroad Avenue and Mill Street. Over $50,000 in holiday prizes will be won at this year’s Midnight Madness.

Be sure to visit St. Michaels the first weekend in December. You don’t want to miss this fun holiday tradition full of good food, great music, and BIG SAVINGS!

The Tall Ships Are Coming To St. Michaels

The Chesapeake Bay Maritime Museum is hosting 5 different tall ships during May & June.  Come and stay at Five Gables Inn & Spa and enjoy our Spa & Sail package which includes two-nights accommodations, a 1-hour massage for 2 people, a 2-hour sail and a dozen crabs at the Crab Claw Restaurant!  Then head to the Chesapeake Bay Maritime Museum to tour a real Tall Ship or a working replica.

When you stay at Five Gables Inn & Spa, you receive $3.00 off regular admission to the museum.  See the schooner Sultana May 5-12, the schooner Wolf June 4-7, the replica of the HMS Bounty June 15-17, The Pride of Baltimore June 21 & 22 and the Viking Ship Norseman June 22-24.

The Bounty’s visit co-insides with the very popular, Antique and Classic Boat Festival at CBMM.  The Bounty was built in 1960 for the movie “Mutiny on the Bounty” and was featured in several television programs and “Pirates of the Caribbean: Dead Man’s Chest”.  This is a great chance to see some of the most beautiful boats on the Chesapeake and its surrounding waters.  Come stay at Five Gables and tour a legend!!

St. Patrick’s Day

St.-Patricks-Day-2St. Patrick’s Day is special this year in St. Michaels, when Carpenter Street Saloon will be holding their Annual Shopping Cart Races on Saturday night, March 17th.  The epitome of small town fun that you just have to see to believe.

Stay at Five Gables Inn & Spa and take a short walk to Carpenter Street Saloon and enjoy the best corned beef and cabbage in town for dinner.  Stay for the festivities and shopping cart races and you don’t worry about driving!


Five Gables Gift Certificates  are the best and easiest presents to buy, give and receive.  Give your spouse or children a stay in one of our fabulous room or suites.  Or, give them a spa treatment at our Aveda Spa.  Without question, your gifts will be the most appreciated this Christmas!

And remember, Five Gables Gift Certificates work for lots of people on your list – family, friends, bosses, teachers, doormen, postmen, UPS drivers – everyone loves a gift certificate from Five Gables.

Christmas In St. Michaels!

Christmas in St. Michaels is a truly fabulous time here in St. Michaels.  Homes and businesses are decked out in Christmas finery.  Enjoy the tour of historic houses, the Craft Bazaar and Gingerbread House display.  The parade on Saturday morning is our favorite.  Stay at Five Gables and share some of John’s award winning eggnog.

Fall In St. Michaels

Fall in St. Michaels is still going on and some of the best events are coming up. Next weekend, children from all over will dress in their spookiest costumes and parade through St. Michaels on Saturday afternoon. If you are a dog lover, there are as many dogs as kids dressed up and parading! Local businesses will be handing out candy to all participants. Of course, at Flying Freds, we will be handing out biscuits for our four legged friends! And, on Sunday, the Carpenter Street Auction is the thing to do. This is an annual event to sponsor the volunteer fire departments of St. Michaels and Tilghman Island. Many of the businesses and local residents donate treasures including lunches and dinners at our fabulous restaurants, treatments at local spas and stays at our hotels, inns and b & b’s. You can bid on wonderful furniture, jewelry and clothing too! You will be amazed at all the things you won’t be able to live without!

On November 5th, Oysters take over the town and the Chesapeake Bay Maritime Museum. The Museum has a full schedule of events from learning how to tong to tasting some of the finest Oyster Stew available. Many of the businesses on Talbot Street will be serving oysters in many variations too. And of course, the retailers will be offering lots of oyster related items.

Fabulous Fall

St. Michaels is fabulous in the Fall.  And, Five Gables Inn & Spa is making Fall even more fabulous. Stay one night midweek and receive the 2nd night ½ off! This special is available Sunday thru Thursday excluding holidays and cannot be combined with any other discounts or packages. Don’t miss out on this very special offer!

Summer in St. Michaels………

Summer in St. Michaels – steamed crabs, sailboat races on the Miles River, the Farmers Market, lazy walks around town, festivals at the Chesapeake Maritime Museum, dinners at fabulous restaurants, shopping in unique boutiques, relaxing afternoons around our indoor pool, a massage or a soak in your own Jacuzzi tub…it doesn’t get any better than spending time at Five Gables Inn & Spa.

Retire to St. Michaels………

Come and stay at Five Gables Inn & Spa to find out why Money Magazine name St. Michaels one of the top 3 cities to retire to.

Experience the laid back charm, historic houses and delicious restaurants first hand.  Tour the Maritime Museum and learn about the Chesapeake Bay.  Take a boat ride on the Miles River or just enjoy a massage, the sauna, steam room and indoor pool during your stay at Five Gables.

Spring into Five Gables Inn & Spa

Spring is a great time to visit St. Michaels!  Daffodils are blooming, window boxes are full of pansies, shops are open and new merchandise is arriving daily, restaurants are offering new menus and new specials.  Everything looks crisp and new.

Five Gables is offering our Spring Package during April.  This package includes two nights for two people, a 1 hour massage each, a spring daffodil basket and chocolates.

This package starts at $440.00 for two nights midweek.