Thanksgiving in St. Michaels

St. Michaels is a popular destination during the summer months because of it’s location on the Eastern shore, but did you know that it is just as beautiful throughout autumn and winter?

St. Michaels is so quaint and beautiful during the fall season, but if you haven’t had the chance to experience it yet, time is running out! Thanksgiving is right around the corner and there is absolutely nothing like spending the holiday season in a small, waterfront town.


Why not spend the post-Thanksgiving weekend with us? Avoid the madness of Black Friday by doing all of your shopping in our charming little town.

Many of our local retailers will be offering Black Friday specials, so you can receive the holiday discounts without all of the insanity you would find in a crowded mall.

We have plenty of openings for the weekend of Thanksgiving, but we expect them to go fast, so be sure to book sooner rather than later!

Call us today!

It’s a Scream of a Deal!

Halloween weekend is right around the corner and St. Michaels is the place to be!

We take the month of October very seriously here in St. Michaels. We have been preparing for Halloween for weeks now. The entire town has been adorned from head to toe in Halloween décor and this weekend is filled with events leading up to the big day! This weekend will feature Pumpkin Carving Contests, Pumpkin Patch Games for the kids, Ghost Tours and much much more!


The main event will be held on Saturday the 30th. St. Michaels will host a Halloween Celebration and Parade! The parade starts at 4pm and Trick or Treating begins at 6! On Sunday afternoon, the St. Michaels Fire Department will host the annual Carpenter Street auction.

At Five Gables, we are offering a great special for the upcoming Halloween weekend. If you book a room for Oct. 29th and 30th, we will take 30% off of our regularly priced rooms! Sorry, no other discounts will apply.

Take advantage of this special and spend this year’s Halloween enjoying the beauty of Fall in St. Michaels!

2010 Jack Russell Terrier Races

Every year, dog owners from all over Maryland join the residents of Talbot County on the lawn at the Inn at Perry Cabin for the annual Jack Russell Terrier Race & Dachshund Dash. This year’s races will being at 11:00 am on Sunday, October 24th. Registration begins promptly at 9:30 that morning.

Take a look at this short video featuring former Jack Russell Racing champ, Beacon.

The proceeds from the benefit will go to the St. Michaels Community Food Bank, which will provide non-perishable and nutritious foods to needy families in Bay Hundred.

The races will be broken down into categories: Jack Russell (flat and hurdles), Norwich, and West Highland. There will also be a Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race.

The even will be held, rain or shine and refreshments will be available on site. Come and help the residents of Talbot County raise money for a local charity! Join us at the 14th Annual Jack Russel Terrier Races!

Trade Spaces with Your Spouse

Wouldn’t it be great if your husband could learn how to cook while you enjoy a relaxing spa experience? Well our Trading Spaces package allows just that.

We have recently created a package that allows couples to spend an interactive and relaxing weekend away from the kids. The men will attend a 2-3 hour cooking class that will involve them in some of the preparation for the evening’s dinner. And ladies, while your husband is slaving away in the kitchen, you will enjoy and “Ultimate” spa package at the inn. At 6:00 p.m., the couples will reunite and sit down at Gourmet by the Bay for a served dinner that will include the items that the men had helped to prepare earlier in the day.
This package will only be offered on four (4) separate weekends throughout the year in order to maximize the experience, so space is very limited. Be sure to book in advance in order to secure a spot.

Upcoming weekends:

Winter January 28/29, 2011
Spring March 11/12, 2011
Summer July 15/16, 2011

Visit our site for more information:

Amenities Galore at Five Gables Inn!

We are proud to offer a wide variety of amenities to match any of our guests needs. The most popular summertime amenity is the complimentary bikes we provide for our guests to explore St. Michaels with. All of our rooms also come with air-conditioning for the summer and fireplaces for the winter. For our guests relaxation we provide Aveda spa products in our bathrooms, each outfitted with a whirlpool tub. The Inn also has a seasonally heated indoor swimming pool, sauna and steam room, as well as 4 pet friendly rooms, so that your dog can stay in comfort with you in our well appointed guest rooms. We are happy to help our guests schedule events for the weekend to make sure they see all that St. Michaels has to offer! Visit us today at to book your weekend getaway!

3rd Annual Chesapeake Bay Maritime Museum Folk Festival

Join us for a weekend of great folk music on the water! This Saturday, July 31st is one of our favorite events of the year in St. Michaels. Our neighbors, the Chesapeake Bay Maritime Museum, are throwing their 3rd annual Folk Festival to, “celebrate the Bay’s people, food, music, work and traditions.” This fantastic event includes boat rides, maritime demonstrations, and even includes events for kids.  The festival runs from 10am to 5pm, which leaves plenty of time to relax and explore St. Michaels. Our Inn is conveniently located in the heart of historic St. Michaels, a short walk to the Maritime Museum and to shopping and restaurants. Take out our complimentary bikes for a Sunday afternoon picnic, the perfect end to a great weekend! Visit to book your weekend getaway.

Holy Smoke Maryland State BBQ Championship in Easton, MD

Join us this Saturday and Sunday on Marlboro Ave in Easton for the 1st Annual Holy Smoke Maryland State BBQ Championship! Admission is just $3, free for kids 10 and under. When you’re tried some of the states best BBQ enjoy some live music by Coffey Anderson, have the kids play on the free air bounce and carnival rides! Even watch a twinkie eating competition! After a day full of BBQ and fun, relax with us in our indoor pool or stop by our Aveda spa for a massage or facial. Make sure to burn off some of that BBQ by taking our complimentary bikes for a spin around St. Michaels! Visit for more information regarding the event. The St. Michaels Community Center is presenting Dan Goggin’s Broadway smash hit “Nunsense” at St. Michaels High School, Thursdays, July 22 & 29 at 7 pm, Fridays and Saturdays, July 23, 24, 30 & 31 at 8 pm and Sundays, July 25 and August 1 at 2 pm. Between the BBQ and the show you will have a jampacked weekend of good food, fun and entertainment on Maryland’s eastern shore!

Featured Package: Spa and Sail

Looking to escape to the Eastern Shore for two nights of relaxation and sailing? Look no further than our special summer package, Spa and Sail. This package includes two night accommodation, two 1-hour massages in our Aveda Spa, a two hour sail plus a $50 gift certificate to The Crab Claw! Package available weekends or weekdays. Please contact us at to reserve. While you’re not on the water explore all St. Michaels has to offer. Visit us between July 19-25 and enjoy Plein-Air Easton, the outdoor painting competition hosted by the Avalon Make sure to check out the Hundred Studio Tour to check out the artists work during the competition.

St. Michaels for FREE!

Looking to explore St. Michaels on a budget? There are plenty of free (or almost free) activities to fill up a whole weekend! Our guests use our complimentary bikes to cruise around historic St. Michaels and window shop, or to take a picnic down to the shore. Spend Saturday mornings roaming the St. Michaels Fresh Farm Market in Muskrat Park, a great park on the water, walking distance to Five Gables Inn, it is also home to Concerts in the Park every Thursday night. Saturday nights in the summer enjoy the free Avalon Summer Concert Series in Easton. Enjoy music from Rock/Blues/Pop to Country and even Afro funk big band. Spend a day exploring the exhibit at the Chesapeake Bay Maritime Museum, $13 for adults but free for kids under 6.

Historic St. Michaels

Aside from being an amazing place to get away, St. Michaels, Maryland has a rich history dating back to the 1770’s. Many of its historic attractions have been preserved and put on exhibit for the public to enjoy. Any historic boat lover will appreciate the Edna E. Lockwood, a Chesapeake Bay bugeye, which is the last working oyster boat of her kind. Built in 1889 on Tilghman Island, she is on display at the Chesapeake Bay Maritime Museum. The St. Michaels Historic District is a great area for any history buff to wander around, taking in the historic integrity of the buildings. Make sure to see The Cannon Ball House, which has a cannon ball embedded in the house from an attack during the war of 1812. Come spend the weekend with us and take in all the history St. Michaels has to offer!