Chestertown Travel Guide

  • Chestertown
    by frankcanfly
  • Sunrise across the river
    Sunrise across the river
    by grandmaR
  • Chestertown from the water
    Chestertown from the water
    by grandmaR

Chestertown Things to Do

  • frankcanfly's Profile Photo

    by frankcanfly Written Oct 20, 2003

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    History comes to life through the annual Chestertown Tea Party, reenacted each Memorial Day weekend.

    This festival celebrates events of May 23, 1774 when, on the heels of the news that the Port of Boston had been closed by the British, local residents boarded the Brigantine Geddes, which had dropped anchor in the Chester, and angrily consigned its shipment of tea to the depths of the River.

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    by frankcanfly Written Oct 20, 2003

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    Chestertown`s shipbuilding past has been revived by the recent Schooner Sultana project. The Sultana, a replica of a traditional 18th century schooner, was constructed locally by a non-profit organization using traditional ship building skills.

    It was launched in May of 2001. The ship serves as a floating classroom offering unique, hands on educational opportunities for children and adults that focus on history and the study of the natural environment.

    This photo was taken in 1999 during construction.

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    by frankcanfly Written Oct 20, 2003

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    Chestertown is also home to Washington College. Washington College is the tenth oldest college in the United States. The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college. Washington served as a trustee and received an honorary degree.

    I personally know two great professors here!

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Chestertown Hotels

Chestertown Restaurants

  • grandmaR's Profile Photo

    by grandmaR Updated Aug 1, 2008

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    I have been informed that this restaurant has gone out of business altogether. VT member cliokent wrote "Reiley's on the River (which opened about May-June 2007) abruptly went out of business in Feb. 2008 (a good thing in my view). A new operation opened in early May as the Fish Whistle. Therefore, it probably would be a good idea if your now out-of-date posting could be deleted entirely, as none of it applies now. When I have more time, I intend to write a Fish Whistle tip myself" I can't tell whether this restaurant is at the same site as the Old Wharf or not. If it is, then SOME of it applies.

    In any case, marina restaurants throughout the east coast of the US (and probably also the world) regularly go out of business, or change chefs and get reinvented as something else. It would be too bad if there was no restaurant at the marina, but not unusual. It's not even unusual for NON-marina restaurants come to think about it. So I will do as I usually do when I find that a restaurant has change and that is to make a note about it in the tip
    ----------------------------
    We went to the Old Wharf Inn (right next to the marina) for dinner. The Old Wharf serves breakfast, brunch, lunch, dinner and has take-out. Fresh seafood daily. Renowned crab bisque.

    Open Monday-Saturday: Lunch 11-4 pm; Dinner 4-Closing. Sunday: Brunch 10-3 pm; Dinner 3-Closing.

    Favorite Dish: I had a crab cake (fried), and Bob had calves liver. For dessert, he had an apple dumpling with rum sauce. He said it had more crust than his grandmother's and that her sauce was a hard sauce (the kind made with butter, sugar and rum) instead of a liquid rum sauce. I had a delicious peach shortcake made the way one should be with a real shortcake and not a sponge cake or a pound cake.

    Sunrise with Logo
    Related to:
    • Road Trip
    • Sailing and Boating
    • Family Travel

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  • kooka3's Profile Photo

    by kooka3 Written Jul 27, 2008

    This is a cute coffeehouse/sandwich shop/bakery. There are several nice couches, armchairs, etc to hang out at. They have a couple breakfast bars and stools, as well. The place is small, but nice

    Favorite Dish: The coffee is very good, and people rave about the pasteries, although I haven't tried them yet.

    They also have a selection of wines that they sell, and you save 15% if you buy 6 at a time.

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  • grandmaR's Profile Photo

    by grandmaR Updated Jul 10, 2008

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    This is a fine dining restaurant. It is closed on Sunday.

    Restaurant Hours
    Monday - Saturday
    Lunch Service Begins at 11:30 - Dinner at 5:00
    Reservations are recommended for weekends and larger parties
    Mastercard - Visa - American Express - Discover

    Favorite Dish: We walked into town and had a late lunch at the Blue Heron. Bob had a very good shrimp sandwich, and I had a crab, spinach, potato and sharp cheddar cheese dish, which was quite good, but I thought the spinach and cheese flavors overwhelmed the crab a bit.

    Their current lunch menu includes

    Our Daily Quiche
    Changing selections fill our homemade crusts.
    Served with a small mixed green salad. 9.00

    Jumbo Lump Crab Frittata
    Bell peppers, steamed spinach, green onions, mushrooms and roasted potatoes.
    Topped with warm cheddar and served with jack cheese sauce. 10.00

    Maryland Crab Cake
    Jumbo lump crab baked and served with lemon beurre blanc and
    garnished with a dollop of red remoulade. 15.00

    Pesto Shrimp and Scallops
    Tossed penne pasta, jumbo shrimp and fresh sea scallops with vine ripe tomatoes,
    basil pesto, garlic and romano cheese. 14.00 Vegetarian version. 8.00

    Oyster Fritter
    In a lemon butter sauce...as featured in "Time" magazine! 11.00

    Sautéed Veal Sweetbreads
    With lemon and capers. 13.00

    Turkey Club
    Honey roasted fresh turkey on toasted whole wheat with applewood smoked bacon, romain hearts and sliced tomatoes. Served with herbed potato salad 9 00

    Chicken Pasta
    Pan seared boneless breast of chicken tossed with penne pasta, artichoke hearts,
    vine tomatoes and fresh oregano in a light cream sauce. 12.00

    Sautéed Chicken Livers
    Prepared with mushrooms, tomatoes, onions in a red wine sauce.
    Served over basmati rice. 9.00

    A blue heron in Florida
    Related to:
    • Food and Dining
    • Sailing and Boating
    • Study Abroad

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Chestertown Sports & Outdoors

  • grandmaR's Profile Photo

    by grandmaR Updated Apr 4, 2011

    2 out of 5 starsHelpfulness

    While you can anchor in the Chester River, there is considerable current up by the bridge, the holding is not good and there are cables under the river which you don't want to hook into.

    So we got a space at the Chestertown Marina. It is right in town, and you can walk to everything. There's also a restaurant there.

    We paid $1.00 a foot which included electricity. Now the rates have gone up.

    Transient Rates

    DAILY
    $1.50/ft/night
    Electric: 30amp-$5.00 | 50amp - $10.00

    WEEKLY
    $5.50/ft/week
    Electric: 30amp - $25.00 | 50amp - $35.00

    Normally the marina owner has a courtesy car, but he was out of town, so Bob had to walk to the shopping center.

    Equipment: Their website says that they have
    * 92 octane gas
    * highest quality diesel fuel
    * a discount marine store
    * block & cube ice
    * sodas and snacks
    * deep water launch ramp
    * 25 ton travel lift
    * outboard/inboard mechanic
    * 48 season & transient slips
    * winter storage [wet & dry]
    * unique shops
    * gourmet restaurants
    * adjacent family restaurant
    * adjacent to the Schooner Sultana (which is since our time)

    They also have a boat ramp, with seasonal and daily rates.

    RosalieAnn at the dock
    Related to:
    • Sailing and Boating
    • Historical Travel
    • Family Travel

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Chestertown Favorites

  • grandmaR's Profile Photo

    by grandmaR Written Aug 3, 2004

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    Favorite thing: When we were in the Inner Harbor Marina, Bob tried to get some fresh veggies for us to eat, but he thought the ones at the little market near the boat were tired and wilted, so he didn't buy any. We left Baltimore and sailed over to Rock Hall to get fuel and anchored. The next day we tried to get in to Queenstown and had a bad running aground experience, so we anchored up the Chester River. The following day we went to Chestertown.

    We walked around in town, but most of the grocery stores there were specialty stores and Bob turned up his nose at them as too expensive. So he walked all the way through town to the shopping center to get food. And he walked back carrying the marketing.

    Fondest memory: We had a pleasant sail up the river watching the changing scenery on the banks. We saw a red fox at one point. I took a picture of this structure which I thought looked strange - it was on the charts as silos. I asked around in town, and they said it had been refurbished as a house or apartments to live in.

    There was a continuous window up the side which I suspect was an elevator. It clearly was no longer a working farm, but at least the open space of the fields are being preserved, at least for the time being.

    Silo house
    Related to:
    • Architecture
    • Eco-Tourism
    • Sailing and Boating

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