Maine Trip · Oliver & Rose

Arrive at the barn studio

Drop bags, get the lay of the land, walk down to the river swing. The Stroudwater neighborhood is historic and walkable — there's a book in the studio called "This Was Stroudwater" worth flipping through.

Walk the Stroudwater River Trail

The trail starts practically at your doorstep. A shaded, wooded path following the Stroudwater River — great for an easy first-evening walk to decompress after the drive. Birds, wildflowers, and the occasional great blue heron. Light and manageable.

Marginal Way cliff walk

A 1.25-mile paved coastal path hugging the rocky Atlantic with 39 benches along the way. Native plants, beach roses, a miniature lighthouse, and stunning ocean views. Starts at Shore Road in Ogunquit and ends at Perkins Cove. One of the best coastal walks in New England — flat and accessible. Bring a windbreaker.

Ogunquit Museum of American Art

Arrived in 1953, the OMAA houses 3,000+ works including pieces by Edward Hopper and Winslow Homer, with rotating seasonal shows. Surrounding it are 3 acres of sculpture gardens with 18 gardens and coastal views of the Ogunquit River. The grounds alone are worth the trip.

543 Shore Road, Ogunquit · Admission ~$12/adult · Open May–October

Explore the cove & galleries

Perkins Cove is a cluster of shops, galleries, and restaurants around a picturesque harbor with a working drawbridge. The Barn Gallery (home of the Ogunquit Art Association, est. 1928) is here, as is the Abacus Gallery for jewelry and handcraft. Good place for lunch with views of the boats.

Beach Plum Farm

The last remaining saltwater farm in Ogunquit — 22 acres with a half-mile loop trail through meadows, dunes, community gardens, the Ogunquit River, and ocean views. Over 50 community garden plots, dozens of flower species, and great birdwatching. Free admission.

Beach Plum Farm Rd, Ogunquit

Portland Museum of Art

One of New England's best regional art museums — a serious collection including Monet, Degas, Renoir, Cassatt, Winslow Homer, Andrew Wyeth, and strong holdings of Maine artists. Winslow Homer: Painter, Etcher opens summer 2026, so the timing is excellent. Free admission on Fridays, but Wednesday is open 10am–6pm.

7 Congress Square, Portland · Wed–Fri 10am–6pm (Fri until 8pm, free)

Portland bookstore crawl

Carlson & Turner is the essential antiquarian stop — old maps, postcards, prints, and a deep Maine section in a classic shop (check their hours, they're not always open). The Green Hand on Longfellow Square is part new, part vintage, with a strong lean toward the weird and wonderful. Print on Congress is for new titles on current topics, with strong staff picks. Sherman's Maine Coast Book Shop is the reliable chain with good curation. Congress Street is also lined with art galleries, vintage shops, and interesting architecture — plan to wander.

Old Port & Meowy Jane

Meowy Jane in the Old Port is a cat-themed adult-use dispensary with live resident cats, a lounge, and a boutique section (candles, books, jewelry). They run daily specials — Fridays are $10 pre-rolls all day, but Wednesday's boutique day gets 10% off non-cannabis items. Staff are known for being genuinely helpful. Note: you can legally use cannabis in private residences only.

While in the Old Port, check out Pinecone + Chickadee for local art and vintage finds, Open House on Congress for mid-century furniture and textiles, and Haberdashery Resale Clothing for curated secondhand.

Meowy Jane: corner of Market St & Commercial St, Old Port

Kennebunk / Arundel antique trail

The Kennebunk/Arundel area has some of the biggest and most packed antique malls in Maine — worth going south from Portland for a morning of serious browsing. Look for Antiques on Nine (a sprawling multi-dealer mall in Kennebunk) and the shops along Route 1 through Arundel. The whole strip is 20–30 minutes south on I-95.

Fore River Sanctuary + Jewell Falls

An 85-acre preserve in Portland — the only natural waterfall in the city, birding spots where salt and freshwater marsh meet, and wooded trails. A good morning walk if you want nature close to home. A pedestrian bridge connects it to the Stroudwater Trail.

Deering Oaks Park + Eastern Promenade

Deering Oaks is Portland's most beloved city park — 55 acres with a rose garden, pond, and mature trees. Afterward, the Eastern Promenade Trail follows a former rail corridor along the shore of Casco Bay with harbor and ocean views the whole way. Good for a long leisurely walk or a run.

Standard Baking Co. for breakfast

Portland's most beloved bakery, a short walk from the Old Port. World-class croissants, morning buns, and seasonal pastries made with local ingredients. Line up early on weekends — Fridays are manageable. Perfect last-morning send-off.

75 Commercial Street, Portland

Last stop: PMA free admission

If you haven't been yet, Fridays are free admission all day at the Portland Museum of Art, and they stay open until 8pm. Even a quick hour before heading south is worth it. Park nearby and walk the Old Port one last time on your way out.

Portland bookstore circuit

• Carlson & Turner — the essential antiquarian shop. Old maps, postcards, prints, deep Maine section. On Congress St near Eastern Cemetery. Check hours before going — not always open.
• The Green Hand — weird, wonderful, vintage and new. Run by Maine College of Art grad Michelle Souliere, who literally wrote Bigfoot in Maine. Longfellow Square.
• Print — new books on current topics with strong staff curation. Congress St.
• Sherman's Maine Coast Book Shop — reliable, well-stocked, Old Port location.
• Portland Museum of Art bookshop — art books, exhibition catalogs, prints. Worth browsing any time you visit the PMA.

Dispensaries

• Meowy Jane (Old Port) — cat-themed, boutique feel, live resident cats, great staff. Daily specials: Mon 10% off with Maine ID; Tue token giveaway; Wed 10% off boutique; Fri $10 pre-rolls; Sat concentrate deals.
• Fire on Fore — established 2018, started medical, now adult-use. On Fore Street.
• All Kind Bodega — woman-owned, emphasis on homemade edibles (gummies, caramels, chocolate bars).
• SeaWeed Co. — 23 Marginal Way, known for quality and knowledgeable staff.

Legal note: cannabis can only be used in private residences. You cannot smoke in the car, outdoors, or in public.

Vintage & secondhand

• Antiques on Nine / Route 1 in Kennebunk–Arundel — biggest concentration of antique malls in the region, ~25 min south. Best for furniture, rugs, Americana, folk art.
• Open House — Congress St, Portland. Mid-century furniture, textiles, well-chosen vintage pieces.
• Pillars — high-end antiques and architectural pieces, farmhouse tables, antique planters. Worth a browse even if you're not buying.
• Haberdashery Resale Clothing Co. — sustainable fashion resale with a sharp eye for quality. Old Port.
• Pinecone + Chickadee — unique gifts, vintage finds, local art. Old Port.

Green spaces

• Beach Plum Farm, Ogunquit — 22-acre saltwater farm with community gardens, over 50 garden plots, wildflowers, dunes, and a loop trail. Free.
• Ogunquit Museum of American Art sculpture gardens — 18 themed gardens with coastal views, surrounding one of the best art museums in coastal Maine.
• Deering Oaks Park, Portland — city park with a rose garden, mature trees, duck pond. Walking distance from the museum.
• Stroudwater trail / Fore River Sanctuary — practically on your doorstep. Wildflowers, river vegetation, birding.
• Coastal Maine Botanical Gardens (Boothbay, ~1 hr north) — 323 acres with 19 ornamental gardens. Worth a day trip if you want something spectacular. Open May–October.

Museums & galleries

• Portland Museum of Art — permanent collection (Hopper, Monet, Homer, Wyeth, Cassatt, Renoir), plus Winslow Homer: Painter, Etcher opening summer 2026. Free on Fridays.
• Ogunquit Museum of American Art — smaller but exceptional, on the ocean with sculpture gardens. $12/adult.
• Maine College of Art galleries — check their summer schedule for exhibitions from faculty and students.
• Congress Street and the Old Port are lined with small commercial galleries — good for a wander any afternoon.

Wildlife & animals

• Meowy Jane dispensary — live resident (adoptable!) cats in a lounge area. Watch out for Betty — she bites.
• Rachel Carson National Wildlife Refuge (~40 min south, near Wells) — coastal marshlands and forests. Prime birdwatching and quiet nature trails.
• Casco Bay ferry to Peaks Island — seabirds, seals visible from the boat. A relaxing half-day island hop from the Old Port waterfront.
• Fore River Sanctuary — great blue herons, songbirds, turtles where salt and freshwater marsh meet.
• The Stroudwater neighborhood itself: Jim and Deb's chickens and pets, herons along the river, abundant birdlife on the Fore River from the bench at the end of the orchard path.

Trails

• Stroudwater River Trail — starts near your Airbnb. 3.3 miles one-way (6.6 out-and-back), shaded, river views, wildflowers, deer.
• Fore River Sanctuary — 85 acres, Jewell Falls waterfall, good birding. Connected to Stroudwater Trail by pedestrian bridge.
• Marginal Way, Ogunquit — 1.25-mile paved coastal cliff walk. Easy, flat, unforgettable.
• Eastern Promenade Trail — paved, 3.5-mile loop along Casco Bay with harbor views. In Portland, south end at Thames Street.
• Beach Plum Farm trail, Ogunquit — 0.5-mile loop through meadows and dunes. Easy and peaceful.

What you paid

• $303.50 × 4 nights = $1,214.00
• Airbnb service fee: $171.39
• Maine occupancy taxes: $124.69
• Total paid (Google Pay, May 4, 2026): $1,510.08

Refund windows

All times are local (Eastern) based on the listing's location.