Scenic Road Trip from Dayton Ohio to Springfield Illinois via Acadia, Maine, and Massachusetts

Day 1: Departure and Travel

Dayton, Ohio to Bar Harbor, Maine on June 23, 2025

8:00am

Start Road Trip

Depart Dayton early to maximize travel time. The drive to Bar Harbor will take approximately 12 hours with stops.
0USD, 12h0m

12:00pm

Lunch Stop in Albany, NY

Stop for lunch at Jack’s Oyster House, open 11 am to 9 pm, known for local seafood and hearty options.
USD30, 1h0m

7:00pm

Check-in at Bar Harbor Hotel

Arrive and check into Bar Harbor Hotel, ideally located for Acadia National Park visits.
USD250, Overnight

8:00pm

Dinner at Side Street Cafe

Enjoy casual Maine-style seafood dishes in a cozy atmosphere. Open until 9:00 pm.
USD40, 1h0m
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Day 2: Acadia Exploration

Bar Harbor, Maine on June 24, 2025

7:30am

Breakfast at Jeannie's Great Maine Breakfast

Start with classic Maine breakfast dishes. Open 7 am to 2 pm.
USD15, 1h0m

9:00am

Acadia National Park Tour

Explore the park by car and short hikes such as Jordan Pond and Cadillac Mountain. Park open 7 am to sunset. Entrance fee USD30 per vehicle.
USD30, 5h0m

2:00pm

Lunch at Jordan Pond House

Famous for popovers and scenic pond views. Open from 11 am to 4 pm.
USD30, 1h0m

3:30pm

Bar Harbor Downtown Stroll

Enjoy local shops, galleries, and the waterfront promenade.
0USD, 2h0m

6:00pm

Dinner at Havana

A vibrant restaurant offering tapas and waterfront ambiance. Open until 9 pm.
USD50, 1h30m
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Day 3: More Acadia

Bar Harbor, Maine on June 25, 2025

8:00am

Breakfast at Cafe This Way

Popular breakfast spot, open from 7 am offering creative options.
USD15, 1h0m

9:30am

Biking Carriage Roads

Rent a bike and ride the scenic carriage roads for 3-4 hours. Rentals open 8 am to 6 pm.
USD30, 4h0m

2:00pm

Lunch at C-Ray Lobster

Casual lobster shack serving fresh lobster rolls and seafood. Open 11 am to 7 pm.
USD25, 1h0m

3:30pm

Shore Path Walk

Leisurely 1.5 mile walk along the waterfront with beautiful views and photo ops.
0USD, 1h0m

5:30pm

Dinner at The Reading Room Restaurant

Upscale dining with creative dishes in an historic building. Open until 9 pm.
USD60, 1h30m
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Day 4: Travel to Camden & Boarding

Bar Harbor to Camden, Maine on June 26, 2025

7:30am

Breakfast at Morning Glory Bakery

Grab delicious pastries and coffee before departure. Open from 7 am.
USD10, 1h0m

8:30am

Drive to Camden

Approximately 2 hour scenic drive along the Maine coast.
0USD, 2h0m

11:00am

Explore Camden Harbor

Short stroll through quaint town and harborside shops before boarding.
0USD, 1h0m

12:00pm

Lunch at Fresh Foods Cafe

Healthy, fresh Maine fare with vegetarian options. Open 11 am to 8 pm.
USD25, 1h0m

2:00pm

Board Windjammer Angelique

Settle in to your sailing vessel for your week-long cruise. Departure at 3:00pm.
Prepaid, 7d0h
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Day 5: Windjammer Cruise

Camden, Maine aboard Windjammer Angelique on June 27, 2025

All day

Sailing and Island Exploration

Enjoy sailing along the Maine coast, visiting scenic points and islands aboard the historic schooner.
Included in cruise, All day
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Day 6: Windjammer Cruise

Maine Coast on June 28, 2025

All day

Sailing and Onshore Activities

Participate in guided hikes, swimming, and local cultural tours on islands along the route.
Included in cruise, All day
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Day 7: Windjammer Cruise

Maine Coast on June 29, 2025

All day

Sailing and Relaxation

Continue enjoying sailing, sunsets, and onboard meals prepared fresh daily.
Included in cruise, All day
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Day 8: Windjammer Cruise

Maine Coast on June 30, 2025

All day

Sailing and Island Visits

Explore the beauty of the Maine coast with opportunities for kayaking and wildlife spotting.
Included in cruise, All day
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Day 9: Windjammer Cruise

Maine Coast on July 1, 2025

All day

Sailing and Socializing

Join in onboard social events and enjoy evenings star gazing on deck.
Included in cruise, All day
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Day 10: Windjammer Cruise

Maine Coast on July 2, 2025

All day

Sailing and Exploration

Last days of cruising with memorable stops and stunning coastal scenery.
Included in cruise, All day
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Day 11: Windjammer Cruise

Maine Coast on July 3, 2025

All day

Sailing and Leisure

Relax before disembarking with scenic views and peaceful sailing.
Included in cruise, All day
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Day 12: Windjammer Cruise & Disembark

Camden, Maine on July 4, 2025

8:00am

Disembark Windjammer Angelique

Complete your week-long cruise and disembark in Camden, Maine by mid-morning.
Included in cruise, 2h0m

10:00am

Breakfast at Boynton-McKay Food Co.

Enjoy artisanal sandwiches and coffee inside this trendy Camden spot. Open 7 am to 3 pm.
USD15, 1h0m

11:30am

Drive to Salem, Massachusetts

Approximate 2.5 hour drive to Salem for sightseeing in this historic coastal town.
0USD, 2h30m

2:00pm

Check into Salem Hotel

Settle in before exploring Salem’s famous historic sites.
USD180, Overnight

3:00pm

Salem Witch Museum

Discover the history of the 1692 witch trials. Open 9 am to 6 pm. Admission USD15.
USD15, 1h0m

4:30pm

Explore Salem Waterfront

Walk the scenic waterfront with shops and cafes open until 6 pm.
0USD, 1h0m

6:30pm

Dinner at Finz Seafood & Grill

A well-reviewed seafood restaurant with fresh local catches. Open till 9 pm.
USD50, 1h30m
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Day 13: Salem & Boston

Salem and Boston, Massachusetts on July 5, 2025

7:30am

Breakfast at Red’s Sandwich Shop

Classic American breakfast spot in downtown Salem. Open 7 am to 1 pm.
USD15, 1h0m

9:00am

Drive to Boston

Short 30-40 minute drive south to Boston for sightseeing and lodging.
0USD, 0h40m

10:00am

Check into Boston Hotel

Choose centrally located hotel near historic Freedom Trail.
USD200, Overnight

10:45am

Freedom Trail Walk

Guided or self-guided 2.5-mile trail visiting 16 historic sites in Boston. Trail open from sunrise to sunset.
USD0, 3h0m

1:30pm

Lunch at Quincy Market

Iconic food hall offering diverse local and international options. Open 11 am to 8 pm.
USD25, 1h0m

3:00pm

Visit New England Aquarium

Experience marine life exhibits. Open 9 am to 6 pm. Admission USD35.
USD35, 2h0m

5:30pm

Dinner at Legal Sea Foods

Famous Boston seafood restaurant near the aquarium. Open until 9 pm.
USD60, 1h30m
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Day 14: Martha’s Vineyard Day Trip

Boston and Martha’s Vineyard, Massachusetts on July 6, 2025

6:30am

Early Breakfast at Hotel

Quick breakfast before departure, hotel dining or nearby cafe options.
USD15, 0h45m

7:15am

Drive to Woods Hole Ferry Dock

Approximate 1.5 hour drive from Boston to Woods Hole for ferry to Martha’s Vineyard.
USD0, 1h30m

9:00am

Ferry to Martha’s Vineyard

Take the 1-hour ferry crossing to Oak Bluffs, Martha’s Vineyard. Ferry runs multiple times a day; book tickets in advance. Cost approx USD20.
USD20, 1h0m

10:00am

Explore Oak Bluffs

Visit colorful gingerbread cottages and quaint shops. Walking tours available.
0USD, 2h0m

12:30pm

Lunch at The Black Dog Tavern

Renowned Vineyard spot offering seafood and American classics. Open 11:30 am to 3 pm.
USD35, 1h0m

1:30pm

Visit Aquinnah Cliffs

Drive to the western cliffs for spectacular views and photographs. Open daily; no admission fee.
0USD, 1h30m

3:30pm

Return Ferry to Woods Hole

Take afternoon ferry back to Woods Hole.
Included in round trip fare, 1h0m

5:00pm

Drive back to Boston

Return drive to Boston to rest for next day’s activities.
0USD, 1h30m

7:00pm

Dinner at The Capital Grille

Elegant steakhouse in downtown Boston with excellent service. Open until 10 pm.
USD70, 1h30m
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Day 15: Provincetown Excursion

Boston and Provincetown, Massachusetts on July 7, 2025

6:30am

Breakfast at Hotel

Enjoy a quick breakfast to prepare for the day trip.
USD15, 0h45m

7:15am

Drive to Provincetown

Approximate 2-hour drive from Boston to Provincetown at Cape Cod's tip.
0USD, 2h0m

9:30am

Explore Provincetown Center

Walk the charming downtown shops and galleries, enjoy beach views.
0USD, 2h0m

11:30am

Visit Pilgrim Monument

Climb or view the tallest granite monument in the U.S., open 9 am to 5 pm. Admission USD20.
USD20, 1h0m

12:30pm

Lunch at The Mews Restaurant & Cafe

Fresh local seafood in a relaxed setting. Open noon to 9 pm.
USD35, 1h0m

1:45pm

Hike in Provincetown Dunes

Explore the natural sand dune trail at Province Lands Visitor Center.
0USD, 2h0m

4:00pm

Drive back to Boston

Return to Boston for evening rest.
0USD, 2h0m

7:00pm

Dinner at Mamma Maria

Upscale Italian dining in Boston’s North End. Open until 10 pm.
USD60, 1h30m
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Day 16: Start Pennsylvania Amish Country

Boston to Bird in Hand, Pennsylvania on July 8, 2025

7:00am

Breakfast at Hotel

Standard hotel breakfast before beginning long drive.
USD15, 0h45m

8:00am

Drive to Bird in Hand, PA

Approximate 6.5 hour drive heading west to Lancaster County Amish area.
0USD, 6h30m

3:00pm

Check-in Bird in Hand Family Inn

Comfortable lodging in the heart of Amish country.
USD150, Overnight

4:00pm

Explore Bird in Hand Village

Walk the quaint village and visit the Bird in Hand Farmers Market, open until 6 pm.
0USD, 1h30m

6:30pm

Dinner at Bird in Hand Family Restaurant

Enjoy traditional Amish and Pennsylvania Dutch comfort food.
USD40, 1h30m
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Day 17: Explore Amish Country

Bird in Hand and Intercourse, Pennsylvania on July 9, 2025

7:30am

Breakfast at Bird in Hand Bake Shop

Famous for fresh Amish baked goods. Open 7 am to 5 pm.
USD10, 1h0m

9:00am

Visit Intercourse, PA

Short drive to Intercourse to explore shops, Amish crafts, and eateries.
0USD, 3h0m

12:00pm

Lunch at The Olde Country Store

A classic Amish-style eatery serving homestyle lunches. Open 11 am to 4 pm.
USD25, 1h0m

1:30pm

Visit Amish Farm and House Tour

Learn about Amish history and lifestyle through a guided tour. Open 9 am to 5 pm. Admission USD14.
USD14, 1h30m

3:30pm

Return to Bird in Hand

Relax or visit local shops.
0USD, 1h30m

6:00pm

Dinner at Good 'N Plenty Restaurant

Hearty Pennsylvania Dutch meals served family-style. Open until 8 pm.
USD40, 1h30m
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Day 18: Paradise and Blue Ball

Pennsylvania Amish Country on July 10, 2025

7:30am

Breakfast at Homestead Bakery

Traditional pastries and simple breakfast fare. Open 7 am to 4 pm.
USD10, 1h0m

9:00am

Drive to Paradise, PA

Explore Paradise town, local shops, and the Amish Country Homestead Museum.
USD12, 2h0m

11:30am

Visit Blue Ball, PA

Stop at the Blue Ball Heritage Center for cultural exhibits and artisan workshops.
0USD, 2h0m

1:30pm

Lunch at Shady Maple Smorgasbord

Large Pennsylvania Dutch buffet open 11 am to 8 pm, great for sampling local cuisine.
USD30, 1h30m

3:00pm

Return to Bird in Hand

Rest and relax at lodging.
0USD, 1h0m

6:00pm

Dinner at Bird in Hand Smokehouse

Casual BBQ and smoked meats with Amish flair.
USD35, 1h30m
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Day 19: Travel to Springfield, Illinois

Bird in Hand, PA to Springfield, IL on July 11, 2025

7:00am

Breakfast and Departure

Early breakfast followed by departure on about an 8-hour drive to Springfield, Illinois.
USD15, 8h0m

12:00pm

Lunch Break in Cleveland, OH

Stop at West Side Market to eat at one of the many stalls offering diverse foods. Open 7 am to 6 pm.
USD20, 1h0m

3:00pm

Continue Driving

Complete the drive to Springfield with possible light stops for breaks.
0USD, 4h0m

7:00pm

Arrive and Check-in Hotel

Settle into hotel in Springfield, such as Hyatt Regency Springfield.
USD150, Overnight

7:30pm

Dinner at Incredibly Delicious

A local favorite known for American casual dining and craft beers. Open until 9 pm.
USD40, 1h30m
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Day 20: Explore Springfield

Springfield, Illinois on July 12, 2025

8:00am

Breakfast at Obed & Isaac's Microbrewery and Eatery

Rustic breakfast menu with local beers brewed onsite. Open 7 am to 2 pm.
USD20, 1h0m

9:30am

Visit Abraham Lincoln Presidential Library and Museum

A premier museum dedicated to President Lincoln’s life and legacy. Open 9 am to 5 pm. Admission USD15.
USD15, 3h0m

1:00pm

Lunch at Cozy Dog Drive In

Famous for corn dogs and classic Americana. Open 11 am to 7 pm.
USD15, 1h0m

2:30pm

Tour Illinois State Capitol

Take a guided tour of this historic government building. Open 9 am to 5 pm with free admission.
0USD, 1h30m

4:30pm

Walk and Relax at Washington Park

Enjoy scenic gardens and outdoor sculptures before the evening.
0USD, 1h0m

6:30pm

Dinner at Maldaner's Restaurant

Upscale dining with seasonal Midwestern cuisine. Open until 9 pm.
USD60, 1h30m
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Day 21: Departure

Springfield, Illinois on July 13, 2025

8:00am

Breakfast and Departure

Final breakfast in Springfield before continuing your onward journey or concluding the itinerary.
USD15, 1h0m
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