01   /   Maryland Avenue, Annapolis

Old Fox Books & Brown Mustache Coffee

35 Maryland Avenue, Annapolis, MD 21401

This is the stop for a morning you’d like to keep mostly to yourself, or a coffee date with someone who will happily spend half an hour looking at books. Brown Mustache Coffee is inside Old Fox Books, where new and used titles share space with stationery and gifts.

The extra reason to go is the garden and patio out back. Choose something you want to read and take the first chapter outside with your drink. A table in a bookstore garden makes a convincing case for leaving your phone in your bag.

Leave some time for Maryland Avenue after you finish. You’re already on a block of independent shops, so this is an easy place to let a coffee date turn into a browse. If it rains, you still have the bookstore to explore.

02   /   Ritchie Highway, Severna Park

Rise Up Coffee, with Homestead next door

522 Ritchie Highway, Severna Park, MD 21146

If your fall plans tend to involve something for the front porch, start here. Rise Up’s Severna Park café is alongside Homestead Gardens, making it easy to pair your coffee with a look through the plants and seasonal décor.

The café has a detail worth looking for, too. Rise Up describes a repurposed bank vault from the building’s previous life, along with indoor and outdoor seating. Mad Eggs serves breakfast and lunch here, so you can eat before you wander next door.

Before you head over, take a photo of the spot at home you’re trying to finish. It gives you something to work from when you start looking at planters or fall color at Homestead Gardens. Of course, you may go in for one plant and find another corner of the porch that needs attention.

This pairing is for Homestead’s Severna Park location. Check the venue and address separately if you’re planning around a Homestead event.

03   /   Olde Severna Park

The Big Bean, then a walk on the B&A Trail

558 Baltimore Annapolis Boulevard, Severna Park, MD 21146

The original Big Bean has Olde Severna Park at its front door and the B&A Trail behind it. Bring the friend you’ve been meaning to catch up with, order something warm, and give yourselves enough time to walk without watching the clock.

There’s a good story behind the shop. Christie Coster worked here as a barista, and Greg was a customer before they started dating. They later married and bought the business in 2019. The Small Business Administration’s profile of the Costers tells how they came to own the coffee shop where they first met.

The county’s B&A Trail guide describes a paved route following the former railroad corridor. For a shorter outing, choose an easy turnaround point and make your way back when you feel like it. Hatton-Regester Green has gardens and benches if you’d rather sit for part of your visit.

04   /   West Annapolis

Bean Rush Cafe and a browse along Annapolis Street

112A Annapolis Street, Annapolis, MD 21401

Choose Bean Rush’s West Annapolis café when you want to get out for coffee and see where the morning goes. Start with something to eat, then leave time to browse nearby. Visit Annapolis’ neighborhood guide pairs this stop with local art and antique shopping.

Owners Mark and Shannon Abrahams worked on private charter yachts in the Caribbean before opening their first café in Crownsville. Their story of starting Bean Rush explains why they later chose West Annapolis: they wanted a small location with character and a sense of community.

This is a good outing to leave open-ended. Look for a gift, spend a little time with the art, or browse the antiques without a shopping list. If you’re meeting someone on Sunday, check the café’s hours first; its posted Sunday closing time is earlier than Saturday’s.