We’re so excited you’ll be joining us in Gloucester! Whether you’re here for a long weekend or just a couple of days, there’s so much to see and do, both right around our venue and in nearby spots like Boston and a favorite of ours, Salem. Here are some ideas to help you make the most of your trip!

If you’re flying in or out of Boston, you might want to spend a little time exploring the city before or after the wedding:

Cheers Bar: A must stop for us every time. Visit the bar that inspired the classic TV show Cheers and snap a photo by the iconic sign.

Green Dragon Tavern: If you want somewhere that feels Boston-y in the old-school sense, the Green Dragon Tavern is perfect. You’re sitting in a tavern that claims, with reason, to have been where the Sons of Liberty plotted, Paul Revere passed through, and where thousands of small steps toward the Revolution happened. This spot is a mix of tourists and locals, which makes it all the better.

Union Oyster House: If you do just one classic Boston restaurant, it should be Union Oyster House. It’s literally living history — the building dates back to the early 1700s, and the restaurant has operated since 1826. The vibe is unmatched: wood booths, an old oyster bar, memorabilia, stories everywhere. Upstairs, you can take a peek at the booth that JFK would always request, a bonus, it has the memorabilia to prove it.

Freedom Trail: A walking route that takes you past Boston’s most famous historic sites.

Boston Public Garden – Take a stroll or hop on a swan boat.

North End: Boston’s “Little Italy,” with amazing pasta, pastries, and coffee. Be sure to check out two of our favorite spots in this area! Mike's Pastry and Cafe Delo. Both are right around the corner from the Old North Church. It is a favorite spot of ours to stop whenever we are in Boston!

USS Constitution: Visiting the USS Constitution & its Museum is like stepping into a piece of U.S. history. You get to walk aboard ‘Old Ironsides’ — an over-200-year-old warship that still belongs to the Navy — and then dig into its story in the museum through interactive exhibits, artifacts, and stories of sailors. It is one of the stops on the Freedom Trail. The surrounding area has cafes and restaurants to explore.

Hammond Castle Museum – A real castle with ocean views, fascinating architecture, and plenty of photo ops. (8 min drive / ~3.5 miles)

https://hammondcastle.org/

Good Harbor Beach – Stunning sandy beach with gentle waves. (7 min drive / ~2.5 miles)



Whale Watching Tours - One of the top-rated whale watching tours is a twenty-minute walk from our venue. Lauren and Sharla did this tour a few years back and had a wonderful time. It's a 4-hour commitment, but well worth it! If you get remotely motion sick, bring Dramamine; the ride out can get bumpy.

https://www.tripadvisor.com/AttractionProductReview-g41580-d11478124-Whale_Watching_Tour_in_Gloucester-Gloucester_Cape_Ann_Massachusetts.html

Additionally, 15 Best Things to Do in Gloucester: https://www.tripadvisor.com/Attractions-g41580-Activities-oa0-Gloucester_Cape_Ann_Massachusetts.html

We couldn't put together a list of fun activities and sites to see when you are out this way without mentioning one of our favorite day stops. Joey and I have made a stop in Salem every time we have come to the Boston area. May will be off-season, and hopefully less crowded. We have compiled a list of our favorite things to do and places to check out in Salem.

Salem Ghosts: Witches, Warlocks, & Hauntings Tour

This walking ghost tour takes you to the most haunted locations in Salem and introduces you to the city’s haunted history firsthand through eerie encounters that lie around every corner.

We did this tour when we were in town to tour our venue. We had such a great time. Tours are available day and night, but we recommend a nighttime tour if you want to get the true spooky vibe. This tour was the perfect blend of spooky storytelling, history, and seeing the best parts of Salem. The extended tour option is worth it if you can fit it in! This is a walking tour, and it is a lot of walking.

https://salemghosts.com/salem-ghost-tour/

This is the link to the company we went through, but there are many in the area.

Salem Witch Museum

If we want something meaningful, haunting, and very Salem-iconic, the Salem Witch Museum is perfect. Learn more about Salem in a dramatic, immersive show about the witch trials, plus a thoughtful exhibit about how images of witches and witch hunts evolved. It’s not super long — about an hour. This is a gimmicky show, but fun and quick to do.

Restaurants We've Loved

The Ugly Mug Diner: Open till 2 pm, and reservations go fast. Serves breakfast and some lunch options. This lovely little diner has the spirit of Halloween, and the food was delicious!

https://www.uglymugdiner.com/

The Ledger: This was such a fun spot that we chose for dinner one night. The space is beautiful, inside a former bank with vintage charm but also modern polish. The food is excellent; you have to get the popovers (Lauren's suggestion). The drink menu is fun and creative, especially if you like cocktails. This was a fun spot for dinner, but it would also be perfect for appetizers and drinks.

https://www.ledgersalem.com/

Rockafellas: it’s got a great mix of upscale casual, tasty food, and a welcoming atmosphere. The building is historic, which gives it character, and the menu has something for everyone (steaks, seafood, comfort foods like the baked mac and cheese), and the portions are good. Plus, the bar’s nice if anybody wants cocktails.

https://rockafellasofsalem.com/

There are many options to grab a drink or a bite to eat in this historic town. Here are some other suggestions:

https://www.bostonmagazine.com/restaurants/best-restaurants-salem/

Calling All Hocus Pocus Fans!!

If you are as big a fan of Hocus Pocus as we are, here are the spots you have to check out while in Salem!

(Some of these locations are fairly wide apart, so we suggest you make this a driving tour. Especially to Max's house, the cemetery, and Old Pioneer Village.)

· Dani & Max’s House (with Iconic Tower!) – 4 Ocean Ave.

· Allison’s House – The Ropes Mansion, 318 Essex Street

· The Cemetery – Old Burial Hill, Marblehead

· The high school – South Washington Square

· Thackery Binx’s House & Old Salem Village (Known as Old Pioneer Village) 98 West Avenue.

· The Halloween Party at Town Hall – Old Town Hall, 32 Derby Square.

· Where Max Flirts with Allison – Salem Commons