Things to Do Around the Chesapeake Bay: Annapolis and the Eastern Shore
This site's Chesapeake Bay hub already covers the region's county-by-county property tax variation, its Critical Area development law, and the blue crab and oyster industries as a genuinely volatile working economy -- none of that gets repeated here. This page does the other job a things-to-do page owes a reader: the real, dated, verifiable attractions across two distinct halves of this market. Annapolis brings a working military academy, the nation's oldest state capitol still in legislative use, and a satirical "secession" that's a real 501(c)(3) nonprofit. The Eastern Shore, a Bay Bridge crossing away, brings a maritime museum with a National Historic Landmark boat and a 340-plus-year-old ferry. Both halves get covered here on their own terms, not folded into one generic "Chesapeake" list -- and where access to a working military installation has genuinely changed in the last few months, that's stated plainly rather than assumed static.
The US Naval Academy: A Real Public Tour, on a Base Whose Access Has Actually Changed This Year
The US Naval Academy is a working military institution, not a museum piece -- founded in 1845, it occupies 338 acres between the Severn River and downtown Annapolis and trains roughly 4,400 midshipmen today. Unlike a purely operational installation, USNA does maintain a real, standing public-visitor program: a Visitor Center just outside Gate 1, and guided walking tours of the historic Yard (including the Chapel and crypt of John Paul Jones) bookable through the Naval Academy Business Services Division and its tourism arm. This is a genuine, bookable public tour, not a once-a-year open-house event.
That said, access here has been unusually volatile in 2026, and it's worth stating plainly rather than assuming the base is always open the way it was a year ago. Following the June 2026 U.S.-Israeli strikes on Iran, the Naval Academy suspended general public visits entirely and tightened gate access under increased force-protection measures. Public visits were reinstated starting May 13, 2026 through Gates 1 and 8, but with mandatory bag checks and magnetometer screening at both gates, random vehicle searches, and REAL ID-compliant identification required for every adult visitor; the base's Trusted Traveler expedited-access program remained suspended as of that reopening. Treat this as a working military base that can restrict or suspend public access again on short notice -- confirm current gate hours and access rules directly at usna.edu/Visit before planning a trip around it.
The Maryland State House: The Nation's Oldest State Capitol Still in Legislative Use
The Maryland State House, construction of which began in 1772 and finished in 1797, is widely documented as the oldest US state capitol still in continuous legislative use -- it still houses the Maryland General Assembly today, more than 250 years after its cornerstone was laid. It carries two additional, specific and verifiable claims: it has the largest wooden dome in the country built without nails, and its lightning rod was reportedly grounded to specifications Benjamin Franklin himself provided.
The building's history reaches beyond Maryland politics. Annapolis briefly served as the national capital in 1783-84, and it happened inside this building: George Washington resigned his commission as commander of the Continental Army in the Old Senate Chamber on December 23, 1783, and the Treaty of Paris, formally ending the Revolutionary War, was ratified there on January 14, 1784. Confirm current tour hours and any General Assembly session-related access restrictions directly with the State House before visiting, since legislative business can limit public areas on session days.
City Dock and the Maritime Republic of Eastport: A Working Waterfront and a Real Satirical "Secession"
City Dock sits on what was once known as "Dock Cove" on Spa Creek, and a public market has operated on the site since 1730 -- making it one of the longer continuously used waterfront market sites in the country, not a modern redevelopment dressed up as historic. It remains the working center of downtown Annapolis: boat slips, waterfront restaurants, and the jumping-off point for harbor tours sit within a short walk of the State House and Naval Academy gates.
Across the water in Eastport, the Maritime Republic of Eastport (MRE) is a real, documented piece of local culture, not just a nickname. It began as a tongue-in-cheek "secession" on Super Bowl Sunday 1998, when Eastport residents worried a planned drawbridge repair connecting their peninsula to downtown Annapolis would isolate local businesses; they "seceded" in jest under the slogan "we like it this way." MRE operates today as a registered 501(c)(3) nonprofit and stages an annual charity Tug of War across Spa Creek -- billed as the longest international tug-of-war over water in the world -- plus a satirical "0.05K Bridge Run." Some informal local talk mentions an MRE currency, passport, or "mayor"; none of that could be independently confirmed, so treat the Tug of War and Bridge Run as the real, verifiable events and the rest as unconfirmed folklore.
America's Sailing Capital: The US Sailboat Show
Annapolis markets itself as "America's Sailing Capital," and the claim has real annual programming behind it. The United States Sailboat Show, held each fall at City Dock, is described by regional boating press as the largest in-water sailboat show in the world, drawing roughly 200 boats in recent years; 2019 coverage marking its "50th year" places its founding around 1969, though this site could not locate a primary founding-date source beyond that anniversary reporting. It now runs alongside a companion Annapolis Powerboat Show under the same organizing group. Confirm current dates directly at annapolisboatshows.com, since fall show scheduling shifts year to year.
The sailing identity runs deeper than the boat show. The Naval Academy's Robert Crown Sailing Center operates a fleet of Navy 44 Mark II training sloops -- Congressionally funded, one-design offshore boats used to teach midshipmen navigation and seamanship, the fourth generation of a purpose-built USNA training fleet dating back to a dozen Bill Luders-designed wooden yawls built after World War II. These are training vessels for midshipmen, not a public charter fleet, but they're a visible, working part of why Annapolis's sailing reputation is substantive rather than just a marketing tagline.
The Chesapeake Bay Maritime Museum in St. Michaels: A National Historic Landmark, Not a Roadside Attraction
Cross the Bay Bridge into Talbot County and the Eastern Shore's flagship attraction is the Chesapeake Bay Maritime Museum in St. Michaels, founded in 1965 on Navy Point. It holds what's described as the world's largest collection of traditional Chesapeake Bay boats, anchored by two genuinely significant vessels: the Edna E. Lockwood, the last sailing log-bottom bugeye on the Bay and a designated National Historic Landmark, and the Rosie Parks, a 1955 skipjack that underwent a restoration beginning in 2009. These aren't replicas built for tourists -- they're preserved working boats from the Bay's actual commercial sailing-oyster-fleet era.
The museum sits directly on the water at Navy Point and anchors the town of St. Michaels the way the Naval Academy anchors Annapolis, but on a smaller, quieter scale. Confirm current hours, admission pricing, and any seasonal exhibit closures directly at cbmm.org before visiting, since museum hours typically shift between peak season and the off-season.
The Oxford-Bellevue Ferry: A 340-Plus-Year Claim, a Recent Ownership Change, and a Real Closure Worth Checking Before You Go
The Oxford-Bellevue Ferry, connecting the Eastern Shore towns of Oxford and Bellevue across the Tred Avon River, is marketed as dating to 1683 and billed as the oldest privately owned and operated ferry in the United States -- a claim repeated consistently across Wikipedia, Talbot County tourism material, and the ferry's own site, and treated here as a well-established marketing date rather than a single-source claim. Worth noting for precision: the ferry's own history page emphasizes specific documented ferry-keeper records from the 1750s rather than restating 1683 directly, so the earliest date is better understood as a long-repeated founding tradition than a single unbroken paper trail back to 1683.
Two more current facts matter more for trip planning than the founding date. First, ownership changed in 2024, when the ferry -- operated for more than two decades by Tom and Judy Bixler, who received a 2020 US Senate commendation as a "Small Business of the Week" -- transitioned to a company called JettyLight. Second, the ferry underwent an unscheduled maintenance closure in mid-2025 with no confirmed reopening date located in reporting from that period. This site could not confirm the ferry's current 2026 operating status as of this research pass -- call the ferry's own line or check oxfordferry.com directly before building a visit around it, rather than assuming it's running on any given day.
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Get a Free Agent Referral →Independent research. No ads. No sponsored listings. The US Naval Academy's 1845 founding, 338-acre campus, and roughly 4,400 midshipmen are drawn from USNA's own fact sheet; its standing public Visitor Center and guided-walking-tour program are confirmed via the Naval Academy Business Services Division and navalacademytourism.com. The 2026 access disruption -- public visits suspended following the U.S.-Israeli strikes on Iran, then reinstated starting May 13, 2026 through Gates 1 and 8 with mandatory bag checks, magnetometer screening, and REAL ID identification requirements, with the Trusted Traveler program still suspended as of that reopening -- is drawn from Eye On Annapolis's February 2026 reporting and a May 2026 Patch report on the resumption; confirm current status directly at usna.edu/Visit before visiting, since this is a live, changeable security posture rather than a settled policy. The Maryland State House's 1772-1797 construction, its status as the oldest US state capitol in continuous legislative use, its nail-free wooden dome, George Washington's December 23, 1783 resignation of his commission there, and the Treaty of Paris's January 14, 1784 ratification there are corroborated across Wikipedia, msa.maryland.gov, and statehouse.maryland.gov. City Dock's origin as "Dock Cove" on Spa Creek and its public market operating since 1730 are drawn from this site's own research memo. The Maritime Republic of Eastport's Super Bowl Sunday 1998 founding, its drawbridge-repair origin story, its status as a registered 501(c)(3) nonprofit, and its annual Tug of War and "0.05K Bridge Run" are documented and real; an MRE currency, passport, or "mayor" could not be confirmed in this research pass and are presented as unconfirmed folklore, not fact. The US Sailboat Show's description as the world's largest in-water sailboat show, its roughly 200-boat scale, and its ~1969 founding (inferred from 2019 "50th year" anniversary reporting rather than a directly located founding-date source) are drawn from Chesapeake Bay Magazine reporting; confirm current dates at annapolisboatshows.com. The Robert Crown Sailing Center's Navy 44 Mark II fleet and its lineage back to a post-WWII fleet of Bill Luders-designed training yawls are drawn from this site's own research memo. The Chesapeake Bay Maritime Museum's 1965 founding at Navy Point in St. Michaels, its claim to the world's largest collection of traditional Chesapeake Bay boats, the Edna E. Lockwood's National Historic Landmark status, and the Rosie Parks's 1955 origin and restoration beginning in 2009 are drawn from the museum's own institutional history; confirm current hours and admission at cbmm.org. The Oxford-Bellevue Ferry's marketed 1683 founding date is corroborated across Wikipedia, Talbot County tourism (tourtalbot.org), and the ferry's own site, though the ferry's own history page emphasizes 1750s ferry-keeper records rather than restating 1683 directly -- treat 1683 as a long-repeated founding tradition rather than an unbroken single-source paper trail. The ferry's 2024 ownership transition from longtime operators Tom and Judy Bixler (a 2020 US Senate "Small Business of the Week" commendation) to a company called JettyLight is drawn from Talbot County Economic Development and Marine Link reporting. A mid-2025 unscheduled maintenance closure with no confirmed reopening date is drawn from WBOC and Star Democrat reporting; this page could not confirm the ferry's current 2026 operating status and treats that as an open gap rather than an assumption -- confirm directly at oxfordferry.com or by phone before visiting. Nothing on this page is legal, financial, or travel advice; hours, admission, gate access, and operating schedules all change and should be confirmed directly with each institution before planning a visit around it.