Exploring the Charm of Old Town Alexandria This Fall

Fall is one of my favorite times to explore Old Town Alexandria. The air turns crisp, the trees along King Street start to glow, and the whole neighborhood takes on that perfect mix of cozy and lively. Whether you’re a local looking for weekend plans or visiting from nearby, Old Town has something for everyone — from great restaurants and shops to seasonal events worth making time for.

🍽️ Where to Eat in Old Town Alexandria This Fall

Old Town’s restaurant scene really shines this time of year — cooler evenings, cozy lighting, and just enough patio weather left to make the most of it. Here are a few of my go-to spots to add to your fall lineup:

Thompson Italian

Tucked right on King Street, Thompson Italian has quickly become a local favorite. Their house-made pastas are incredible (don’t skip the rigatoni or their famous desserts). The atmosphere strikes that perfect balance — casual enough for a weeknight dinner, but polished enough for a special night out.

Perfect for: Date night or a slow Sunday dinner.

Ada’s on the River

If you want dinner with a view, Ada’s on the River is hard to beat. It sits right on the waterfront, and the outdoor seating lets you take in the fall colors reflecting off the Potomac. The menu focuses on wood-fired dishes — think grilled steaks, seafood, and roasted vegetables — with a cozy, upscale feel.

Perfect for: A sunset meal or a celebratory brunch with friends.

BARCA Pier & Wine Bar

Before the weather turns too chilly, grab a table outside at BARCA. It’s a lively spot right on the water with a mix of Spanish-inspired tapas, cocktails, and great people-watching. Come for the sangria, stay for the views.

Perfect for: Afternoon bites or drinks by the water.

Landini Brothers

A true Old Town classic. Landini Brothers has been serving authentic Tuscan food since the 1970s, and it’s one of those places that always feels special without trying too hard. The service is warm, the pasta is excellent, and the bar feels timeless.

Perfect for: A cozy fall evening or family dinner.

Josephine

Josephine brings a modern French twist to Old Town. The design is beautiful — soft lighting, vintage details — and the food feels comforting but elevated. Their brunch is one of my favorites in the area, especially paired with a latte or a mimosa.

Perfect for: A relaxed brunch or a quiet mid-week dinner.

🛍️ Where to Shop in Old Town Alexandria

Between the cobblestone streets, historic charm, and locally owned storefronts, Old Town makes it easy to spend a fall afternoon shopping. Whether you’re looking for home décor, a special gift, or something to refresh your wardrobe, here are a few favorites worth stopping by.

Crème de la Crème

This boutique feels like stepping into a little slice of Paris. Crème de la Crème is filled with beautiful home accents, ceramics, and European-inspired gifts — the kind of pieces that instantly elevate a room. It’s perfect for fall entertaining touches or a thoughtful hostess gift.

Perfect for: Unique home décor and one-of-a-kind finds.

Red Barn Mercantile

If you love cozy textures, warm colors, and interiors that tell a story, Red Barn Mercantile is a must. They carry everything from pillows and rugs to candles and stationery — all curated with that “Old Town charm meets modern design” feel.

Perfect for: Home décor, gifts, and fall-inspired accents.

Bishop Boutique & ERA

These sister stores are staples on King Street. Bishop Boutique focuses on women’s clothing, accessories, and shoes — polished but approachable pieces you’ll actually wear. Right next door, ERA offers more elevated, trend-forward styles with that “editor off-duty” look.

Perfect for: Updating your fall wardrobe or finding the perfect statement piece. 

J. Brown & Co.

For design lovers, J. Brown & Co. is a local gem. It’s a beautifully curated home and lifestyle store filled with everything from furniture and lighting to seasonal décor and gifts. Even if you’re not shopping for anything specific, it’s one of those stores you’ll want to wander through for inspiration.

Perfect for: Home design ideas and luxury décor pieces.

🍂 Fall Events & Weekend Tips

Fall in Old Town Alexandria is truly something special — crisp air, tree-lined streets glowing in gold and red, and a packed calendar of local events that make the neighborhood feel alive. Whether you’re planning a weekend visit or enjoying your own backyard, here are a few can’t-miss happenings from late October through Thanksgiving.

Trick-or-Treating on Lee Street

Every Halloween, Lee Street turns into one of the most charming (and festive) blocks in the DMV. The historic rowhomes go all out with decorations, and the street fills with families, kids in costume, and neighbors handing out candy.

Perfect for: Families and anyone who loves a little old-fashioned Halloween magic.

Ghost & Graveyard Tour

The Ghost & Graveyard Tour winds through Old Town streets by lantern light, sharing stories of hauntings and local history. Fall evenings make it extra atmospheric — a spooky yet educational outing.

Perfect for: A fun date night or something unique with visiting friends.

Old Town Farmers’ Market

Saturday mornings at 301 King Street are made for strolling through fresh produce, baked goods, and local crafts. Fall adds pumpkins, seasonal flowers, and that perfect crisp air.

Perfect for: Slow Saturday mornings and casual weekend plans.

Alexandria Fall-O-Ween at John Carlyle Square

A family-friendly festival with crafts, treats, and live entertainment — a relaxed way to celebrate the season.

Perfect for: Families and casual fall fun.

Alexandria Cider Festival (Sat Nov 22)

Sample Virginia ciders, enjoy live music, and soak in the historic setting surrounded by peak fall color.

Perfect for: Couples, small groups, and anyone who loves local food and drink.

Women’s History Walks – Alexandria Celebrates Women

Guided walks exploring stories of the women who shaped the city’s history. A thoughtful way to enjoy the season while learning something new.

Perfect for: History buffs and those who love a purposeful stroll.

Specialty Tour: “Poisons” at the Apothecary Museum

A quirky, offbeat look at 19th-century medicine that pairs well with a downtown stroll and a meal nearby.

Perfect for: A fun twist on a classic museum visit.

Weekend Tips

• Arrive early for markets, tours, and Lee Street.

• Dress in layers — fall evenings can be crisp.

• Use Old Town’s walkable layout or trolley to avoid parking stress.

• Plan a full day: Farmers’ Market → brunch → shopping → evening event.

• Reserve tickets ahead for popular events like the Cider Festival.

• Bring your camera — King Street and the waterfront look amazing this time of year.

Closing Thought:

With so many ways to experience Old Town this season — from cozy brunches and boutique shopping to festive events and historic tours — fall weekends here offer the perfect mix of relaxation and exploration. Whether you’re wandering tree-lined streets, sipping cider by the waterfront, or strolling through a local market, there’s always a new corner to discover. Pair your outings with one of the restaurants or shops mentioned earlier, and you’ve got a full, memorable weekend that captures the charm, community, and seasonal magic of Old Town Alexandria.