Itinerary for my 4th trip to Washington DC

Question

Hello All,

My solo trip to Washington DC is rapidly approaching and it will be my 4th visit to the capital. I am planning a bit of the off-the-beaten-path itinerary this time but will certainly revisit my all time favorites (see my next post please). Staying at the Residence Inn Dupont Circle and taking Acela train from Boston.

I will be very grateful for your expert advice and more recommendations. I have only four days this time.

Thank you in advance,

Nora

Answer

Hi Nora — that sounds like a wonderful trip in the making! Since this is your fourth time in D.C. and you’re staying in Dupont Circle, I think leaning into more “off-the-beaten-path” places is a perfect plan. Below is a suggested 4-day itinerary focused on hidden gems, quieter neighborhoods, and some less-touristed museums — plus food, walks, and other curiosities.

Day 1 — Arrival & Dupont Circle / Kalorama

Stroll the Spanish Steps — Right in your neighborhood, the elegant Spanish Steps (22nd St NW) are tucked away and feel very local and peaceful.
O Street Museum — Visit the Mansion on O Street: this quirky place has over 100 rooms and 80 secret doors, with art, rare books, music memorabilia, and more. Make a reservation for a self-guided tour.
Dupont Architecture Walk — Explore the elegant mansions around Dupont, including the Patterson Mansion. Also check out the Codman Carriage House nearby.
Dinner in Dupont: pick a cozy café or bistro on 17th or 19th Street — the area is rich in charming, independent dining spots. (Ask locals or your hotel for current recommendations.)

Day 2 — Hidden Museums & Quiet Corners

Phillips Collection — Head to this beautiful, more intimate modern art museum in Dupont / Logan Circle. It’s less crowded, and the collection is excellent.
Anacostia Community Museum — This Smithsonian museum tells powerful stories about community life in D.C., and it’s in a part of the city many tourists don’t reach.
Kenilworth Aquatic Gardens — For a break from the cityscape: these tranquil lotus and water lily ponds are a serene natural escape.
Big Chair in Anacostia — On your way out, stop by the iconic “Big Chair,” a quirky public art piece and neighborhood landmark.
Dinner option: Try something in Anacostia or head back toward Capitol Hill — exploring the food scene in residential neighborhoods can be very rewarding.

Day 3 — Architecture, Gardens & Secret Spots

Dumbarton Oaks Gardens — Located in Georgetown, this historic garden and small museum feels like a refuge. It’s particularly lovely for slow walks, contemplation, and art.
Bartholdi Fountain & Gardens — Near the U.S. Botanic Garden, this is a peaceful, under-the-radar spot with beautiful landscaping.
Kogod Courtyard — Inside the National Portrait Gallery / Smithsonian American Art Museum building, this quiet glass-roofed space is a great place to pause, read, or people-watch.
Summerhouse by the Capitol — A small, tucked-away stone pavilion on the Capitol grounds — perfect for a quiet, reflective moment.
Evening: Dine in Georgetown or head back to Dupont for a cocktail in a cozy bar.

Day 4 — Quirky History & Departing Time

Lincoln’s Cottage — Visit the “Home for Brave Ideas”: this was Lincoln’s retreat during the Civil War. It's a little off the tourist map and deeply meaningful.
Theodore Roosevelt Island — Walk the trails on this wooded island in the Potomac; a peaceful nature break in the city.
Textile Museum — In a charming, lesser-known spot, this museum has fascinating exhibits on fabric, fiber arts, and design.
Ford’s Theatre & Museum — Explore the place where Lincoln was assassinated, and the museum around it.
If you have time before your train: perhaps grab a farewell lunch or coffee in a Dupont Circle café, then take a final walk through local embassies or along 22nd Street to revisit favorite corners.

Extra Tips & Considerations

Reservations: For places like O Street Museum or Lincoln’s Cottage, check ahead and reserve — some spots require online booking.
Walking pace: Since these are more “hidden” or local spots, you’ll want to move deliberately and take breaks; part of the joy is lingering.
Transport: Use Metro + Lyft / Uber to get between quadrants; Dupont Circle is very well connected so you can easily reach Anacostia, Georgetown, and the Mall.
Weather: December weather in DC can be chilly and unpredictable — dress in layers, and pack comfortable walking shoes.

Why This Itinerary Works for Your 4th Trip

You’ve likely seen the major icons (the Mall, big Smithsonian museums), so this plan gives you a fresh perspective — exploring residency-scale views, community history, gardens, and architecture. It’s slow, thoughtful, and deeply local. It also plays to your base in Dupont Circle, so you’re not constantly shifting hotels or scrambling across tourist zones.