Northeast Road Trip: 40 Days of Culture, Nature, and Discovery
Embark on the ultimate 40-day adventure across five vibrant Northeastern cities—Wilmington, Bridgeport, Providence, Boston, and Portland—starting and ending in Cumberland, MD. With 7–8 days in each location, explore world-class museums, historic districts, waterfront views, and unforgettable food scenes. Whether it’s wandering scenic gardens, cruising coastal bays, or strolling charming old towns, this itinerary blends relaxation, culture, and exploration at every turn. Bonus: scenic return stops in Portsmouth, Albany, and Gettysburg.
Wilmington, DE
Experience a mix of rich history and modern flair. Visit the grand Nemours Estate, walk the Riverfront, and explore the lush landscapes of Longwood Gardens. Wilmington offers a serene yet sophisticated introduction to the Northeast. Activities: Nemours Estate Delaware Art Museum Wilmington Riverfront Brandywine Zoo Longwood Gardens (nearby) Hagley Museum Meals: Breakfast: Sleeping Bird Coffee / Hotel Lunch: Iron Hill Brewery / Bardea Lunch Dinner: Bardea Food & Drink / Le Cavalier / Merchant Bar
Bridgeport, CT
A family-friendly hub on the Connecticut coast with coastal parks, aquariums, and cultural museums. Enjoy hands-on fun at Discovery Museum and unwind at Seaside Park with views of Long Island Sound. Activities: Beardsley Zoo Discovery Museum & Planetarium Seaside Park Captain’s Cove Seaport Housatonic Museum of Art Fairfield Museum Meals: Breakfast: Harborview Market / Hotel Lunch: Local Cafés / Food Trucks Dinner: Bereket Turkish Restaurant / Tazza Osteria & Bar
Providence, RI
An artsy city bursting with energy. Visit the RISD Museum, dine along Federal Hill, and witness the magic of WaterFire. Providence fuses colonial charm with creative modern culture. Activities: RISD Museum Roger Williams Park & Zoo Benefit Street/College Hill WaterFire (if scheduled) Federal Hill dining Rhode Island State House Meals: Breakfast: Ellie's Bakery / Hotel Lunch: East Side Pockets / Local Delis Dinner: Hemenway's / Al Forno / Oberlin
Boston, MA
America’s historical heart—walk the Freedom Trail, catch a game at Fenway, and indulge in culinary gems from the North End. Boston delivers a perfect balance of tradition, innovation, and East Coast energy. Activities: Freedom Trail walking tour Museum of Fine Arts Fenway Park tour or game Boston Tea Party Ships & Museum Boston Common & Public Garden Newbury Street shopping Meals: Breakfast: Tatte Bakery & Café / Hotel Lunch: Legal Sea Foods / Quincy Market Dinner: Mamma Maria / Neptune Oyster / Toro
Portland, ME
A coastal gem with lighthouses, lobster, and local charm. Stroll through Old Port, ferry out on Casco Bay, and hike the Eastern Promenade for sweeping views. Portland is your chill, scenic finale. Activities: Portland Head Light Portland Museum of Art Casco Bay Ferry Ride Old Port district Eastern Promenade Day trip to Freeport (L.L. Bean HQ) Meals: Breakfast: Holy Donut / Standard Baking Co. Lunch: Duckfat / Bite Into Maine Dinner: Street & Co. / Scales / Central Provisions
Cozy Cafes
Start days at Tatte Bakery in Boston, Holy Donut in Portland, and Ellie's in Providence.
Local Dinning
Dine at Le Cavalier (Wilmington), Union Oyster House (Boston), and Duckfat (Portland).
Boutique Stays
Sleep in charm and style—from The Quoin in Wilmington to The Newbury in Boston.
Hidden Gems
Try Bardea Food & Drink or Street & Co.—local favorites with flavor and flair.
🚗 Local Transportation
Navigate cities with ease—most stops are walkable or have great public transport. Your own car is best for coastal and small-town flexibility.
💳 Currency & Payments
USD is accepted everywhere. Use cards for ease, but keep cash for tolls or small eateries.
🚨 Emergency Tips
911 for emergencies. Have roadside assistance (AAA or similar), and check hospital locations in each major stop.
🌎 International Traveler
No visa needed for U.S. citizens. International visitors may require an ESTA or tourist visa—plan in advance.