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5-Day Road Trip: From Summerville, SC to Portland, ME (Sept 18–22, 2024)

Viewed by 55 travelers

Day 1: Drive North

Summerville, SC > Richmond, VA on September 18, 2024

7:30am

Breakfast at Page's Okra Grill (Summerville)

Local favorite for Southern breakfast classics—hearty plate to fuel a long driving day and a taste of Lowcountry cuisine.
USD18, 1h0m

8:45am

Stroll Historic Downtown Summerville / Azalea Park

Quick 45–60 minute walk through picturesque downtown Summerville and Azalea Park, great for photos and a short stretch before hitting I-95 north.
USD0, 1h0m

9:45am

Depart Summerville for Richmond

Drive north on I-26 to I-95; plan one main driving block with a midpoint rest/lunch stop—total drive ~6.5–7.5 hours depending on traffic.
USD0, 6h30m

1:00pm

Lunch stop (highway break)

Midway highway stop for a quick sit-down or reliable chain option to save time; refuel both car and travelers for the afternoon leg.
USD15, 0h45m

4:30pm

Arrive and check in (Richmond, VA)

Check into a central Richmond hotel; use this time to rest and freshen up before an evening stroll in the Fan or along the James River.
USD140, 1h0m

6:30pm

Dinner at Lemaire (Jefferson Hotel)

Seasonal American fine dining in a historic setting—great for a celebratory first-night dinner (reservations recommended).
USD60, 1h30m

Day 2: History Stop

Richmond, VA > Philadelphia, PA on September 19, 2024

8:00am

Breakfast at Perly's (Richmond)

Popular deli-style spot with hearty breakfast options—good neighborhood energy before a morning museum visit.
USD20, 1h0m

9:30am

Visit the Virginia State Capitol / Monument Avenue

Short visit to Thomas Jefferson–designed State Capitol and a drive or walk past Monument Avenue; museums and grounds typically open mid-morning (check specific exhibit hours).
USD0, 1h30m

11:15am

Depart Richmond for Philadelphia (I-95 N)

Head north on I-95. Expect about a 5.5–7 hour drive depending on traffic; plan a late-afternoon arrival in Philly.
USD0, 6h0m

1:30pm

Lunch stop in Baltimore Inner Harbor (Miss Shirley's Café recommended)

Break the drive in Baltimore—enjoy a flavorful local brunch-style lunch and a quick Inner Harbor stretch if time allows (Miss Shirley's is popular for Southern-Maryland comfort fare).
USD20, 1h0m

5:30pm

Arrive and check in (Philadelphia, PA)

Check into a centrally located hotel (Center City) to make evening strolls and dinner easy.
USD160, 0h45m

7:30pm

Dinner at Zahav

Modern Israeli cuisine and mezze—an acclaimed spot (book well in advance); excellent way to sample local dining culture.
USD65, 2h0m

Day 3: Philadelphia Sightseeing

Philadelphia, PA > New York, NY on September 20, 2024

8:00am

Breakfast at High Street on Market

Excellent bakery/café for artisanal breads, pastries, and creative breakfast dishes to fuel a museum morning.
USD18, 1h0m

9:30am

Visit Independence Hall & Liberty Bell Plaza

Core American history sites—Independence Hall tours typically run mornings through mid-afternoon (free timed tickets recommended for Independence Hall).
USD0, 2h0m

12:00pm

Lunch at Reading Terminal Market

Iconic indoor market with dozens of vendors—sample Philly specialties (cheesesteak, Amish baked goods, or international options).
USD20, 1h0m

1:30pm

Drive to New York City

Shorter driving block north on I-95/I-278 depending on routing—expect roughly 2–2.5 hours (traffic can vary near NYC).
USD0, 2h0m

4:00pm

Arrive and check in (New York City)

Check into a Manhattan hotel (Lower Manhattan or Midtown recommended to minimize local traffic hassles).
USD280, 1h0m

6:30pm

Dinner at Momofuku Noodle Bar or Katz's Delicatessen

Choose Momofuku for refined ramen/noodle dishes (reservations helpful) or Katz's for a classic NYC pastrami experience—both represent very different but iconic NYC meals.
USD30, 1h30m

Day 4: City to Coast

New York, NY > Portland, ME on September 21, 2024

8:00am

Breakfast at Jack's Wife Freda

Mediterranean-inspired breakfast/brunch spot with lively flavors and solid coffee—great neighborhood start before a park walk.
USD22, 1h0m

9:30am

Quick walk in Central Park or High Line

Choose a 60–90 minute stroll (Central Park for classic NYC green space, High Line for elevated urban views) to experience a bit of the city before the long drive.
USD0, 1h30m

11:30am

Lunch at Shake Shack or local deli

Casual, quick lunch to pack up and hit the road; Shake Shack locations are quick and reliable for grab-and-go.
USD15, 0h45m

12:30pm

Depart NYC for Portland, ME

Longest driving day (roughly 5–6.5 hours depending on traffic and border-state speeds); follow I-95 N through Connecticut and Massachusetts into Maine—plan rest stops in southern New England.
USD0, 6h0m

6:30pm

Arrive and check in (Portland, ME)

Check into a waterfront or Old Port hotel and relax after the long drive; expect to arrive in the evening depending on traffic.
USD170, 0h45m

8:00pm

Dinner at Eventide Oyster Co.

Famed for fresh oysters and a modern lobster roll twist—perfect introduction to Portland's seafood scene (reservations or early arrival recommended).
USD50, 1h30m

Day 5: Explore Portland

Portland, ME on September 22, 2024

8:00am

Breakfast at The Holy Donut

Start the day with Maine's famous potato donuts and coffee—casual, delicious, and locally beloved.
USD10, 0h45m

9:30am

Drive to Portland Head Light (Fort Williams Park)

Visit Maine's most photographed lighthouse with dramatic Atlantic views; grounds are open daylight hours—excellent morning light for photos.
USD0, 1h30m

11:30am

Return to Old Port

Wander cobblestone streets, browse shops and galleries, and enjoy the maritime atmosphere of the historic waterfront district.
USD0, 1h0m

12:30pm

Lunch at J's Oyster or Street & Co.

Classic local seafood spot offering clam chowder, fried clams, and oysters—ideal for sampling regional flavors.
USD25, 1h0m

2:00pm

Casco Bay Lines Ferry / Island Cruise (optional)

Take an afternoon ferry or scenic cruise to one of the nearby islands (schedule varies—Sept runs through prime season; check Casco Bay Lines for departure times).
USD20, 2h0m

4:30pm

Afternoon shopping & gallery hopping in Old Port

More time to explore boutiques, local breweries, and art galleries—relaxed pace to round out the trip.
USD0, 1h30m

7:00pm

Dinner at Fore Street

Seasonal, wood-fired cooking showcasing Maine ingredients—excellent final-night dining experience (reservations strongly recommended).
USD65, 2h0m

9:30pm

Evening: Final stroll on the waterfront

Enjoy a calm final walk along the harbor or a nightcap at a downtown pub—quiet end to a scenic northbound road trip.
USD0, 0h30m
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