Long Weekend: Fall in Annapolis, Maryland

Keith took me with him again to Annapolis for a long weekend. I posted some photos on my Instagram… Did you catch my first outfit post from our trip? It was such a fun time going back with him during the fall, my first time there was back in the summer. Here’s a summary of our fun visit, including some info on what to do in Annapolis, Maryland!…


We got into Annapolis from Chicago during the early evening. Before heading to Keith’s Annapolis house, we went for dinner at this super yummy Mexican restaurant called Sin Fronteras Café. I ordered a chicken burrito and a strawberry margarita. After dinner, we went to the house, and Keith had his bandmates over for a jam session. His band is called, The Control.




Keith and I woke up and headed to Iron Rooster for breakfast. Then we spent the early afternoon cruising on his motorcycle, enjoying the warmer day in the city. We drove up near Lancaster, Pennsylvania because Keith and his band were playing a show at this really cool Halloween place called Field of Screams. Field of Screams is a place with a bunch of haunted houses and hayrides and carnival stuff… I went in one haunted house and on the haunted hayride… I was terrified. Keith loves that kind of stuff and had a lot of laughs!










We went for breakfast at this iconic place in downtown Annapolis called Chick & Ruth’s. It looks like a little dive spot, but it’s great! The place was on that Food Network show, Man Vs. Food, because they have a 10lb milkshake! We had breakfast, and it was delicious. The owner was around really livening up the place with his personality. It was a great time. We spent a lot of the day just exploring Annapolis, including going to this pretty area to check out the bay and changing leaves called Quiet Waters Park. At night, we went out with some of his buddies to downtown Annapolis, we went to a few places around the town including Metropolitan Rooftop, Pussers Caribbean Grille, and Charlie’s Pizza Bar.








Was our last day in Annapolis, and a very lazy day! We went downtown for a “bacon brunch” at Dry 85. I had the Stuffed Gypsy Toast… so good…still thinking about it… like so good… since it was NFL Sunday, we mostly chilled at the house with the games on. At night we had a pizza and watched a horror movie, because… Halloween is in less than a week! We got back into Chicago on Monday morning…back to the grind!

What are your Halloween plans/costume ideas? I’m thinking Tiki Girl… Alena decided she wants to be a vampiress! I’m still in mild shock that she has no interest in the fairy princess costume stuff, but it’s cool… she gets to dress up as whoever she wants for the holiday!

With Style & Love,




  1. Amber, it sounds like you and Keith had a blast, that is wonderful. I hope you have a fabulous Halloween… my youngest likes to dress up as zombies and what not too… go figure… I’d want to be the princess xox

  2. Wow, you guys have visited so many (yummy) places. I love mexican food, one of my faves. ;D Gorgeous impressions, babe! So nice to see you sharing the same interests like your love: music, fashion and food – what else can one ask for? :)
    Have an another fabulous weekend, Amber!

    xoxo Ira

  3. sahra

    Oh what fun! I’ve been to Annapolis a few times (it’s so close to me!) but have never been to Iron Rooster. Maybe next time I’ll check it out!

    XO Sahra
    Que Sera Sahra

  4. You two are way too cute! It looks like you really enjoyed yourself! That burrito looked so yummy and the park and scenery looks so gorgeous, I love being around and connecting with nature. It’s so tranquil!

    Thanks for sharing your experience with us and I hope you have an amazing day and weekend ahead, beauty!



  5. Lenya

    Sounds like you had an amazing weekend. Gorgeous pics, Amber. Hope your Halloween weekend was fun. I think it’s so cute that Alena wants to be a vampiress, shows she has a mind of her own, if you know what I mean. Happy new week, girl.

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