What it is: One of the oldest and biggest agricultural fairs in New England — carnival rides, giant pumpkin weigh-offs, livestock shows, food, entertainment.

Why go: If you want a full-on fair vibe (rides, fair food, animals, old-school charm), this is the go-to. Great option for the whole family to have some fun!

Notes: We recommend buying tickets ahead of time through their website. The fair is extremely popular locally and can be crowded at times.

What it is: Salem goes all-in on October with events, festivals, markets, haunted-history tours, and general autumn/Halloween celebration vibes.

Why go: If you want a spooky-but-fun kind of weekend: walking tours, artisan markets, street parades and lots of seasonal energy. Great for anyone!

Notes: Salem gets very busy this time of year, so plan parking, museum visits, tours (or other reservations) ahead of time. For the full experience, expect to walk quite a bit! The commuter rail station is a walkable distance from Essex St. and can offer an easy route in/out of the city.

While you're there, check out Village Tavern, Notch Brewing, or Finz for some food or drinks!

What to do: Pumpkin shopping or apple picking, orchard touring, baked goods, and seasonal family-friendly fall events like hayrides and activities for kids.

Why go: It’s a little less “theme-park busy” than some of the bigger farms, and can be a more relaxed way to enjoy fall vibes.

What it is: A charming waterfront district filled with art galleries, local shops, and seaside restaurants set along a narrow, walkable peninsula. Perfect for a quick coastal stroll with great views and classic New England charm. There are many food options nearby for a quick bite or drinks.

Why Go: You’ll find a mix of independent galleries, handmade jewelry, nautical-themed gifts, souvenirs, art pieces, prints, and more — all in a quaint, coastal-town atmosphere. Great if you like browsing unique, local-maker shops.

Notes: You get there via the town’s Dock Square / Main Street area, then walk onto the Neck peninsula

Newbury Street & Back Bay/Boston Common

Stroll the brownstone-lined streets, grab coffee, shop boutiques, or people-watch at outdoor cafés. We love Buttermilk & Bourbon, Life Alive, and many others! Walk into the common to see the heart of the city.

Faneuil Hall / Quincy Market

Classic Boston—street performers, quick bites, and easy access to historic sites nearby. Walk down the Rose Kennedy greenway if you have the chance, Boston spent a lot of money on this...

North End (Italian District)

Great for dinner (or just cannoli). Hanover Street is lively and cozy in the fall. We love Carmelina's, Trattoria il Panino, Florentine Cafe and Bacco.

Seaport District

Waterfront bars, great seafood, rooftop spots, and pretty sunset views over the harbor. Check out Envoy Rooftop for great views, F1 Arcade for racing fun, or stroll through the shops. Stop by Kanes donuts before heading into the seaport for some good donuts.

Isabella Stewart Gardner Museum

A stunning, courtyard-centered museum that feels like stepping into a different world. Book tickets ahead of time!

Museum of Fine Arts (MFA)

One of the best art museums in the country—big, quiet, and perfect for a few hours indoors.

Boston Common → Beacon Hill Walk

A quick, scenic stroll up through the Common and Public Garden into Beacon Hill’s picturesque brick streets. When you are in Beacon Hill, stop into their unique Tatte or The Sevens for a Narragansett.

Notes: Look for garage parking through the SpotHero app for a significant discount. Take the "T" or walk most places.