Affordable Romantic Fall Honeymoon in Oregon Including Travel from Indiana

Day 1: Travel & Portland Intro

Portland, Oregon on September 22, 2025

5:00am

Drive from Crawfordsville to Indianapolis International Airport

Begin your honeymoon with a 1h20m drive (approx. 70 miles) to Indianapolis airport for your flight to Portland.
USD40 fuel + parking, 1h20m

7:00am

Flight Indianapolis to Portland

Catch a morning flight to Portland International Airport (1 stop), flight approximately 5-6 hours including layover.
USD350 per person round trip, 5h

1:30pm

Check-in at budget-friendly hotel in Portland: McMenamins Crystal Hotel

Stay at this romantic hotel with historic charm downtown, offering good value and a relaxed vibe.
USD120/night, N/A

3:00pm

Afternoon stroll through Portland’s Pearl District

Explore art galleries, boutique shops, and enjoy a casual walk around this trendy neighborhood.
Free, 2h

6:00pm

Dinner at Deschutes Brewery Portland Public House

Dine on locally brewed beer and Northwest fare in a cozy yet lively atmosphere perfect for honeymooners.
USD50, 1.5h
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Day 2: Columbia River Gorge Hike

Columbia River Gorge, Oregon on September 23, 2025

7:30am

Breakfast at Mother’s Bistro & Bar

Enjoy hearty, comfort food breakfast early to fuel a day of hiking.
USD20, 1h

9:00am

Drive to Columbia River Gorge

A 45-minute drive east takes you to stunning waterfalls and hiking trails.
USD10 fuel, 45m

10:00am

Hiking Multnomah Falls and adjacent trails

Explore the famous waterfall and enjoy panoramic views at no cost, open daily dawn to dusk.
Free, 3h

1:00pm

Picnic lunch with groceries from Portland

Save costs and enjoy a romantic picnic at the falls by picking up sandwiches and snacks from a local grocery on the way.
USD20, 1h

3:00pm

Visit local dispensary in Hood River

Explore cannabis shops with local products, mindful to consume responsibly in Oregon’s legal framework.
USD50, 2h

6:30pm

Return to Portland & dinner at Grassa

Enjoy affordable, delicious Italian pasta downtown after a full day outdoors.
USD40, 1.5h
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Day 3: Willamette Wine Region

Willamette Valley, Oregon on September 24, 2025

7:30am

Breakfast at Blue Star Donuts

Indulge in gourmet donuts and coffee for a quick cost-effective breakfast.
USD15, 0.5h

8:00am

Drive to Willamette Valley

Head south approximately 1.5 hours to reach the scenic wine country.
USD15 fuel, 1h30m

10:00am

Wine tasting at Sokol Blosser Vineyard

Enjoy a guided tasting at one of the most historic and affordable vineyards in the region.
USD25 tasting, 1.5h

12:00pm

Lunch at a local deli

Opt for a casual, budget-friendly lunch with fresh sandwiches to save on costs but enjoy local flavors.
USD20, 1h

1:30pm

Visit more vineyards or scenic spots with free access

Explore Willamette Valley’s picturesque towns and free walking trails, perfect for an afternoon of relaxed romance.
Free, 3h

5:30pm

Stay overnight at a cozy Airbnb in McMinnville

Book an affordable, charming Airbnb to enjoy privacy and save on accommodations.
USD100/night, N/A

7:00pm

Dinner at farm-to-table bistro

Dine at a local bistro focusing on seasonal ingredients with moderate prices.
USD50, 1.5h
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Day 4: Willamette Valley Relaxation

Willamette Valley, Oregon on September 25, 2025

8:00am

Breakfast at a nearby cafe

Enjoy a light, affordable breakfast in McMinnville before another day of relaxation and exploration.
USD15, 1h

9:30am

Self-guided vineyard walk and picnic

Visit free-to-access vineyards and enjoy a relaxing romantic walk, followed by a picnic sourced at a local market.
USD25 picnic supplies, 3h

1:00pm

Afternoon at the Allison Inn & Spa facilities (public areas)

Relax in the ambiance of the Inn’s gardens and common areas without booking expensive spa treatments to save budget.
Free, 2h

3:30pm

Explore McMinnville's historic downtown

Enjoy boutique shopping and local artisan galleries in a quaint atmosphere perfect for couples.
Free, 2h

6:30pm

Dinner at Community Plate

Savor a creative, affordable dinner with an emphasis on local produce in a cozy setting.
USD45, 1.5h
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Day 5: Transfer to Bend

Bend, Oregon on September 26, 2025

7:30am

Breakfast at the Airbnb

Prepare a light breakfast to start your day as you drive towards Bend.
USD10, 0.5h

8:00am

Drive to Bend, Oregon

Enjoy scenic 3-hour drive to Bend through Oregon’s varied landscapes.
USD25 fuel, 3h

11:30am

Lunch at Over Easy Cafe

A popular stop in Bend offering hearty breakfast-style dishes perfect for a midday meal.
USD20, 1h

1:00pm

Visit Smith Rock State Park

Famous for rock climbing and hiking, enjoy moderate trails and spectacular views (parking fee $5), open dawn to dusk.
USD5, 3h

5:00pm

Check-in at budget hotel in Bend: The Oxford Hotel

Affordable, comfortable lodging located near downtown, perfect for honeymooners.
USD110/night, N/A

7:00pm

Dinner at Zydeco Kitchen & Cocktails

Enjoy Cajun comfort food and creative cocktails in a lively, romantic setting.
USD45, 1.5h
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Day 6: Bend Outdoor Adventure

Bend, Oregon on September 27, 2025

8:00am

Breakfast at Chow

Known for farm-fresh, creative breakfast dishes that offer a great start for a day outdoors.
USD15, 1h

9:30am

Hiking at Tumalo Falls

Easy to moderate hiking with beautiful waterfall views. The park opens 7am–7pm, parking $5.
USD5, 2h

12:00pm

Lunch at Barrio

Enjoy Latin street food-style fresh dishes at reasonable prices in a fun downtown atmosphere.
USD25, 1h

1:30pm

Relax or shop downtown Bend

Browse galleries, boutiques, or relax at coffee shops in the pedestrian-friendly downtown.
Free, 2h

4:00pm

Visit local cannabis dispensary

Explore Bend’s vibrant dispensary scene and select legal recreational cannabis products.
USD40, 1.5h

7:00pm

Dinner at Ariana Restaurant

Celebrate your final evening with creative seasonal cuisine in a warmly romantic setting, budget-conscious dining.
USD60, 2h
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Day 7: Return Travel Home

Portland, Oregon to Crawfordsville, Indiana on September 28, 2025

7:00am

Breakfast at Thump Coffee

Enjoy a quick, quality coffee and pastry before leaving Bend.
USD15, 0.5h

7:30am

Drive from Bend to Portland Airport

Approximate 3-hour drive back to Portland airport for your return flight.
USD25 fuel, 3h

11:00am

Flight Portland to Indianapolis

Return flight to Indianapolis International Airport (1 stop), roughly 5-6 hours.
Included round trip, 5h

5:00pm

Drive from Indianapolis Airport to Crawfordsville

Arrive back home after 1h20m drive (approx. 70 miles), concluding your budget-friendly romantic honeymoon.
USD40 fuel, 1h20m
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