30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland vacation planner
©
Make it your trip
Drive
1
Havre de Grace
— 2 nights
Drive
2
Ocean City
— 6 nights
Drive
3
Cambridge
— 3 nights
Drive
4
Stevensville, Kent Island
— 1 night
Drive
5
Annapolis
— 5 nights
Drive
6
Solomons
— 3 nights
Drive
7
Cumberland
— 4 nights
Drive
8
Frederick
— 5 nights
Fly

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Havre de Grace — 2 nights

Havre de Grace, abbreviated HdG, is a city in Harford County, Maryland, situated at the mouth of the Susquehanna River and the head of Chesapeake Bay. Step off the beaten path and head to Susquehanna State Park and Havre de Grace Promenade. Change things up with these side-trips from Havre de Grace: Elk Neck State Park (in North East) and Ladew Topiary Gardens (in Monkton). There's lots more to do: see human ingenuity at work at Conowingo Dam, examine the collection at Steppingstone Museum, and meet the residents at Plumpton Park Zoo.

To find maps, ratings, more things to do, and tourist information, read Havre de Grace driving holiday app.

New York City to Havre de Grace is an approximately 3-hour car ride. Plan for a bit cooler nights when traveling from New York City in November since evenings lows in Havre de Grace dip to 37°F. Finish your sightseeing early on the 3rd (Wed) so you can travel to Ocean City.
Parks · Nature · Zoos & Aquariums · Historic Sites
Side Trips

Ocean City — 6 nights

One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Explore hidden gems such as Northside Park and Assateague State Park. You'll find plenty of places to visit near Ocean City: Salisbury (Pemberton Historical Park, Salisbury Zoo, &more). The adventure continues: get a new perspective on things with Boat Tours & Water Sports, indulge your thirst for a good beer at Burley Oak Brewing Company, get outside with Ayers Creek Adventures, and tee off at Rum Pointe Seaside Golf Links.

To see reviews, where to stay, other places to visit, and tourist information, refer to the Ocean City trip app.

Getting from Havre de Grace to Ocean City by car takes about 2.5 hours. In November, plan for daily highs up to 57°F, and evening lows to 39°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Cambridge.
Parks · Outdoors · Tours · Historic Sites
Side Trips

Cambridge — 3 nights

Cambridge is a city in Dorchester County, Maryland, United States. Explore hidden gems such as Blackwater National Wildlife Refuge and 1879 Hooper Strait Lighthouse. Change things up with a short trip to Spas in St. Michaels (about 36 minutes away). There's still lots to do: take an in-depth tour of Harriet Tubman Museum and Educational Center, get all the information you need at Harriet Tubman Underground Railroad National Historical Park, and look for gifts at The Amish Market.

To find photos, reviews, where to stay, and other tourist information, read our Cambridge trip planner.

Traveling by car from Ocean City to Cambridge takes 1.5 hours. Expect a daytime high around 57°F in November, and nighttime lows around 39°F. Finish up your sightseeing early on the 12th (Fri) so you can go by car to Stevensville.
Museums · Parks · Wildlife · Shopping
Side Trips

Stevensville, Kent Island — 1 night

Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, and is the county's most populous place among both CDPs and municipalities. Start off your visit on the 13th (Sat): get answers to all your questions at Chesapeake Heritage & Visitors Center, then hike along Terrapin Nature Park, and then sample the fine beverages at Blackwater Distilling & Tavern.

To see ratings, maps, where to stay, and more tourist information, go to the Stevensville trip planner.

Traveling by car from Cambridge to Stevensville takes an hour. Expect a daytime high around 55°F in November, and nighttime lows around 41°F. Finish your sightseeing early on the 13th (Sat) so you can drive to Annapolis.
Parks · Wildlife · Trails · Breweries & Distilleries
Side Trip

Annapolis — 5 nights

Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.
Eschew the tourist crowds and head to Hammond-Harwood House and St. Anne's Church. Step out of Annapolis with an excursion to Dutch Country Farmers Market in Laurel--about 40 minutes away. The adventure continues: trek along Quiet Waters Park, cast your line with Family Fishing Adventures, savor the flavors at Fishpaws Marketplace, and explore the activities along Ego Alley.

To find photos, ratings, traveler tips, and tourist information, you can read our Annapolis road trip planner.

Annapolis is just a stone's throw from Stevensville. In November, daily temperatures in Annapolis can reach 56°F, while at night they dip to 42°F. Finish your sightseeing early on the 18th (Thu) to allow enough time to drive to Solomons.
Historic Sites · Parks · Outdoors · Shopping
Side Trips

Solomons — 3 nights

Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. You'll explore the less-touristy side of things at Calvert Marine Museum and Drum Point Lighthouse and Annmarie Garden. Step out of Solomons with an excursion to Janes Island State Park in Crisfield--about 1h 15 min away. There's still lots to do: learn about all things military at Patuxent River Naval Air Museum, trek along Flag Ponds Nature Park, and browse the exhibits of Historic St. Mary's City.

To see reviews, ratings, maps, and other tourist information, refer to the Solomons journey maker tool.

Traveling by car from Annapolis to Solomons takes 1.5 hours. In November, daily temperatures in Solomons can reach 58°F, while at night they dip to 40°F. Finish your sightseeing early on the 21st (Sun) so you can travel to Cumberland.
Museums · Parks · Shopping · Trails
Side Trips

Cumberland — 4 nights

Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. You'll explore the less-touristy side of things at Paw Paw Tunnel and FireFly Farms Market. Get out of town with these interesting Cumberland side-trips: Oakland (Deep Creek Lake State Park & Swallow Falls State Park). There's much more to do: make a trip to Sideling Hill Welcome Center, contemplate the long history of Spruce Forest Artisan Village, immerse yourself in nature at Rocky Gap State Park, and grab your bike and head to Great Allegheny Passage.

To find more things to do, photos, where to stay, and other tourist information, use the Cumberland trip itinerary app.

You can drive from Solomons to Cumberland in 3.5 hours. Traveling from Solomons in November, plan for slightly colder nights in Cumberland, with lows around 34°F. Finish up your sightseeing early on the 25th (Thu) so you can travel to Frederick.
Parks · Nature · Historic Sites · Shopping
Side Trips

Frederick — 5 nights

Frederick is a city and the county seat of Frederick County in the U.S. state of Maryland. You'll explore the less-touristy side of things at Historic Downtown Frederick and Carroll Creek Linear Park. Explore Frederick's surroundings by going to Billy Goat Trail (in Potomac), National Shrine Grotto of Lourdes (in Emmitsburg) and The Adventure Park at Sandy Spring (in Sandy Spring). Next up on the itinerary: get engrossed in the history at National Museum of Civil War Medicine, contemplate the waterfront views at C&O Canal Trust, trek along Catoctin Mountain Park, and see a show at Weinberg Center for the Arts.

To find maps, traveler tips, and tourist information, you can read our Frederick online trip itinerary planner.

Getting from Cumberland to Frederick by car takes about 1.5 hours. In November, daytime highs in Frederick are 56°F, while nighttime lows are 35°F. Finish up your sightseeing early on the 30th (Tue) so you can catch the flight back home.
Parks · Nature · Trails · Historic Sites
Side Trips

Maryland travel guide

4.1
Casinos · Specialty Museums · Aquariums
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.